Stessa Review: The Free Tier Is Real. So Is the $28 Wall Behind It.

Stessa is the default answer to "what should I use to track my rentals" in every landlord forum on the internet, and I understand why: the free plan tracks unlimited properties, pulls your bank transactions automatically, and costs nothing. I know the appeal firsthand, because Stessa is what I used before I gave up and built the thing I actually wanted. I build a competing app, so read this with that bias on the table. But my bias runs toward the truth here: Stessa's free tier is real, and the wall behind it is real too. The free plan is the buffet. The stuff that makes the buffet worth eating is upstairs, and upstairs starts at $28 a month.

If you are still working out how to track rental income and expenses at all, start there first. This review assumes you know what you need the software to do and want to know whether Stessa actually does it.

Quick answer: Stessa Essentials is a genuinely useful free tier (unlimited properties, automatic bank feeds, basic reports, rent collection), but the three things a serious landlord needs most are all paywalled: Schedule E requires Manage at $12 a month, more than 5 receipt scans a month requires Pro at $28 a month, and organizing expenses by project (the thing that determines repair-vs-improvement at tax time) is Pro-only too. I used Stessa before building Doortrackr, and the $28 Projects paywall is the specific reason I quit.

What is Stessa?

Stessa is a rental property finance platform owned by Roofstock, launched in 2016. You connect your bank accounts, mortgage accounts, and credit cards, and it pulls transactions in automatically, categorizes them against real-estate-specific categories, and turns the stream into property-level reports and tax-ready exports. It also has online rent collection, tenant screening, vacancy advertising through Zillow, lease templates, and an interest-bearing cash management account through Thread Bank, per Stessa's pricing page and feature docs.

The pitch is bookkeeping that happens by itself. The money moves, the software watches, the books write themselves. That is a genuinely attractive pitch, and for the most basic version of the job (what came in, what went out, which house did it belong to) it mostly delivers. The problems start where the basic version ends.

What does Stessa actually cost?

The pricing page lists three tiers, all with unlimited properties. Verified live on August 21, 2026:

Plan	Price	What you get	What is gated
Essentials	$0	Unlimited properties, automatic bank feeds, basic financial reports, online rent collection, vacancy marketing, tenant screening, maintenance tracking, 5 receipt scans/month	No Schedule E report, no project tracking, no advanced reports, 5-scan cap
Manage	$12/mo annual, $15 monthly	Everything in Essentials plus the Schedule E report, lease templates, 60+ legal forms, 1 eSignature/month, accelerated rent payments	Still 5 receipt scans/month, still no project expense tracking, still basic reports only
Pro	$28/mo annual, $35 monthly	Everything in Manage plus unlimited receipt scanning, project expense tracking, all advanced reports, budgeting and pro-forma, unlimited portfolios, 7 eSignatures/month, priority phone support	Nothing meaningful

Three things worth saying plainly. First, the free tier is not a demo. Unlimited properties and automatic bank feeds at $0 is more than most of the category gives away, and if all you need is a categorized transaction list, Essentials can carry a small landlord a long way.

Second, the tier structure is built so the thing you came for is always one tier up. You came for tax reports: Schedule E is Manage. You came to scan receipts: unlimited scanning is Pro. You came to group a renovation's expenses together: Projects is Pro. The free tier is genuinely free, and it is also genuinely not the product in the ads.

Third, Manage is the trap tier. It gives you the Schedule E report, which makes it feel like the tax-tier. But it keeps the 5-scan receipt cap and still has no project tracking, so the landlord who upgrades for taxes and then tries to actually capture receipts hits the second wall a week later. You are paying $12 a month for a product that still cannot do the two things this article is about.

The 5-scan cap: the free tier's quiet ceiling

Every plan below Pro caps smart receipt scanning at 5 per month, per Stessa's pricing page. Five. A landlord with three properties who replaces a water heater, buys paint for a turnover, picks up a furnace filter, and makes two hardware-store runs in a month has already blown the cap. I have months where I hit five receipts by the second week.

You can still enter transactions manually past the cap, and bank-feed transactions still import. But the receipt image, the actual proof of the expense, the thing you will want when the IRS or your accountant asks, is now a manual upload attached by hand, or it lives in your camera roll until you forget about it. The cap does not stop you from tracking expenses. It stops you from capturing receipts at the moment they happen, which is the entire point of receipt tracking.

This is the same lesson I learned carrying a wallet full of paper: the longer a receipt sits uncaptured, the more likely it is to fade, tear, or lose its context. A scanner that stops working on the sixth of the month is not a scanner. It is a countdown.

What does the $28 Pro tier actually buy you?

Here is the part I can speak to directly, because this is the wall I hit.

Before I built Doortrackr, I ran my own rentals on Stessa. The free tier worked fine until I tried to do the one thing that matters at tax time: group expenses by the project they belonged to. A bathroom remodel is not twelve random expenses. It is one job, and the difference between a repair you deduct this year and an improvement you depreciate over its recovery period (27.5 years for the building and structural work, 5 for appliances and carpets, 15 for land improvements, per IRS Publication 527) depends entirely on that grouping.

Stessa calls this Projects. I went to use it and found it was locked behind Pro. I could not believe it costs $28 a month just to combine expenses into projects. That is $336 a year for a folder.

I paid it, because I needed it. And here is the part that still annoys me: even after upgrading, actually using Projects was not straightforward. The UI is complicated, the feature is hard to find, and the workflow for assigning expenses to a project (and then deciding repair vs capital improvement) was, in my experience, way too complicated. The reports were the same story. I could not believe how complicated the reports were. My honest estimate: expect a full weekend of learning before you are doing actual bookkeeping in Stessa, and that is after you have paid for the tier that unlocks the feature you needed.

That experience is the reason Doortrackr exists. Not because Stessa is bad software, but because the thing I needed most (group the receipts by the job, at the moment I spend the money, without a taxonomy exam) was locked, buried, and complicated all at once.

Does the automation actually save you time?

Mostly not, and this is the part no review page tells you because it requires having felt it.

Stessa's whole pitch is that the bank feed does the work. Connect your accounts, transactions flow in, machine learning categorizes them. And it does categorize them, often well. But a bank feed automates exactly one thing: it tells you that $847 left your account at Home Depot and which property it roughly belongs to. It does not scan the receipt. It does not attach the photo. It does not tell you whether that $847 was the water heater repair you deduct this year or the kitchen remodel you depreciate, and it cannot, because the receipt is where that context lives.

So every auto-imported transaction still needs you to open it, check the category, and attach the receipt by hand. That is not less work than entering the expense once, correctly, when it happens. It is the same work, scheduled for later, when you have forgotten what the receipt was for. I have done both. Entering it in the moment is faster and the record is better.

Worth being fair here: Stessa's categorization engine is real machine learning trained on years of rental transactions, and it is plausibly the best in the category at guessing that a Home Depot charge is a repair, per independent technical reviews. If your plan is to reconcile a queue of auto-imported transactions once a month and you are disciplined about it, the automation does help. My experience was that the queue became the thing I dreaded, and the discipline decayed, and then I was back to a shoebox with a login screen.

What about the bank connection problems?

This is the complaint you find everywhere once you look, and it matters more here than anywhere because the entire product starts at the bank feed. Stessa's sync runs on Yodlee rather than Plaid, and user reviews across Trustpilot and Reddit describe connections to smaller banks and credit unions staying broken for months, per documented review roundups. When the feed breaks, the automation story breaks with it, and you are back to manual entry inside a tool that was designed around not doing manual entry.

Support is the other recurring complaint: multiple reviewers describe phone support as effectively unreachable even on paid plans, with first-available callback appointments weeks out, per the same review roundups. I did not hit a broken feed in my own time on the platform, so I will not claim that experience. But the pattern is consistent enough across enough independent sources that you should go in knowing the automation has a single point of failure, and it is not one Stessa controls.

What does Stessa genuinely do well?

Credit where it is earned, because some of this is real:

• The free tier is the most generous in the category. Unlimited properties, unlimited bank feeds, basic reports, rent collection, tenant screening, all at $0. Nobody else gives that away. Not us, not Baselane, not Landlord Studio.
• The categorization engine is genuinely good. Real ML, trained on real rental transactions, honestly labeled. When the feed works, it works.
• Schedule E reports exist and are correct once you pay for them. The Manage-tier tax package produces a real Schedule E mapped to the right lines, per Stessa's pricing page.
• Rent collection is solid. Automated reminders, late fees, tenant autopay, and a tenant ledger, included even on Essentials.
• The cash management account pays real interest. Up to 1.88% APY on lower tiers, up to 3.24% on Pro, per Stessa's pricing page, though the highest rates are gated by both plan and balance.
• Unlimited properties on every plan. Most competitors cap properties or charge per unit. Stessa does not.

Where does Stessa fall short?

• Schedule E is paywalled. The one report every landlord exists to file costs $12/month. The free tier tracks your taxes but will not show you the tax form.
• Receipt scanning caps at 5/month below Pro. The single most important capture habit in landlord bookkeeping, rationed.
• Projects is Pro-only and hard to use. The feature that determines repair-vs-improvement at tax time costs $28/month and, in my hands-on experience, was buried and complicated even after I paid for it.
• The learning curve is real. Expect a weekend before you are doing actual bookkeeping, not the 30 seconds the marketing implies.
• Bank sync is a single point of failure. Yodlee connections to smaller banks are a documented, recurring complaint. When the feed breaks, the product's core promise breaks with it.
• Support is slow even on paid plans. Weeks-long waits for phone callbacks are a pattern across independent reviews.
• No job-level context on the receipt itself. Even on Pro, the receipt and the project live in different mental models. The context that determines tax treatment is not captured at the moment of the expense.

Stessa vs the field: true cost for a 3-property landlord

What a landlord with three units actually pays per month for receipt capture plus a Schedule E report plus the ability to group expenses by project, on comparable annual billing:

Tool	What the headline says	What it actually takes	True cost
Stessa	"Free"	Schedule E needs Manage ($12/mo); unlimited scans need Pro ($28/mo); Projects need Pro	$28/mo for the full job
Doortrackr	$6.99/mo flat	Everything unlocked on every tier: unlimited receipt scanning, Schedule E, jobs, no bank switch, no gates	$6.99/mo (Plus, up to 5 properties)
Baselane	"Free banking + books"	Schedule E free on Core; AI tagging + receipt matching need Smart at $20/mo; no job grouping on any tier	$20/mo + your bank account
Landlord Studio	"Free (Go)"	Receipt scanning AND Schedule E both gated to Pro; per-unit escalator past 3 units	$12/mo annual at 3 units
RentRedi	$12/mo annual	Real double-entry books (REI Hub) cost +$25/mo at 1-3 units	$37/mo with real books
QuickBooks	$38/mo (Simple Start)	Not landlord-native; Schedule C-shaped; your CPA still re-maps everything	$38/mo + setup burden

The honest summary: Stessa's $0 Essentials is the best free tracking tier in the category on paper, and if your only ask is a categorized transaction list, it wins. But the version of Stessa that does what a serious landlord needs (captures receipts, produces the tax form, groups the remodel) costs $28 a month, and at that price the comparison changes. For the full head-to-head across every tool in this table, see Best Accounting Software for Rental Property. For the banking-first alternative, our Baselane review covers the same true-cost math from the other direction.

So who is Stessa right for?

Genuinely: a landlord with one or two properties, simple bookkeeping, no major projects, and the discipline to manually review a bank-feed queue once a month. If that is you, the free tier is the best deal in the category and I will not talk you out of it.

Everyone else should read the tier map before signing up. If you have a turnover, a remodel, or a repair-vs-improvement question in your future (and if you own rentals, you do), the thing that answers it costs $28 a month and comes with a learning curve I would not wish on a Saturday. If you collect more than five receipts in a month, the free scanner stops scanning. And if your bank is a credit union, check the Yodlee connection complaints before you build your books on the feed.

The landlord Stessa is wrong for is the one it markets to hardest: the small DIY landlord who wants the receipts sorted, the taxes handled, and the projects grouped, without a weekend of setup and a $336 annual bill for the privilege of a folder. That landlord is who I built Doortrackr for, because that landlord was me.

The bottom line

Stessa is the most honest free tier in landlord software and the least honest $28 tier. The free plan is real, the automation is real when the feed holds, and the categorization is the best in the category. But the product is designed so that everything you actually came for (the tax form, the receipt scanner that works all month, the project folder) sits one tier above wherever you are. I know because I climbed: free, then Manage, then Pro, and the thing I needed was still complicated when I got there.

If you want the receipts captured, attached, and grouped by the job they belonged to, without the rationing, the paywall, or the weekend of learning, that is the exact reason I built Doortrackr: AI receipt scanning on every plan, every expense organized by property and by job, Schedule E reports from the free tier up, $6.99 a month flat with nothing gated. Rental property bookkeeping made stupid simple, at doortrackr.com.

Frequently asked questions

Is Stessa really free?

The Essentials plan is $0 with no time limit and unlimited properties, and it includes automatic bank feeds, basic reports, rent collection, and tenant screening. The catches: Schedule E requires Manage at $12/month, receipt scanning caps at 5/month below Pro, and project expense tracking requires Pro at $28/month.

What is the difference between Stessa Manage and Pro?

Manage ($12/month annual) adds the Schedule E report, lease templates, and legal forms but keeps the 5-receipt-scan monthly cap and has no project tracking. Pro ($28/month annual) removes the scan cap, adds project expense tracking, unlocks all advanced reports, and adds priority phone support. For a landlord who needs receipts plus taxes plus project grouping, Pro is the only tier that does the full job.

Is Stessa good for taxes?

Partially. Stessa produces a real Schedule E report mapped to the correct lines, but only on the $12/month Manage tier and above. The free tier tracks your income and expenses all year but will not generate the tax form. If your accountant files from a Schedule E, budget for the paid tier.

Does Stessa work with any bank?

Stessa connects through Yodlee, which covers most major US banks. The documented complaints concentrate on smaller banks and credit unions, where connections can stay broken for months. If your bank is not a major national institution, verify the connection works before building your bookkeeping on the feed.

Stessa vs Baselane: which is better for a small landlord?

They are different products. Stessa is accounting-first: deeper ML categorization and the best free tracking tier, but Schedule E costs $12/month and unlimited receipt scanning costs $28/month. Baselane is banking-first: Schedule E is genuinely free on Core, but the AI automation costs $20/month and there is no job grouping on any tier. Both run on Thread Bank, so deposit safety is a wash, per this head-to-head teardown.

Is Stessa worth it in 2026?

The free tier is worth it for a 1-2 property landlord with simple needs and monthly reconciliation discipline. The paid tiers are harder to justify: $28/month for Pro buys the receipt scanning and project grouping that Doortrackr includes at $6.99, and Stessa's learning curve and support complaints are well documented. If you need what Pro does, compare the true cost against Doortrackr's flat pricing before committing.

---

Doortrackr is rental property bookkeeping made stupid simple: AI receipt scanning, property and job organization, and IRS-ready Schedule E reports, free for one property and $6.99/month flat after that. Try it free.

Disclosure: I build Doortrackr, which competes with Stessa for small-landlord bookkeeping, and I used Stessa for my own rentals before building it. Everything above was verified against Stessa's live pricing page on August 21, 2026, and my own experience on the platform; where marketing pages and my experience disagreed, my experience is stated as such. Support and bank-sync complaints cited are documented in public reviews (Trustpilot, Reddit, BiggerPockets) and linked inline.