Stoopkeep vs Stessa: The Honest Comparison for Independent Landlords (2026)
Stessa raised its prices and buried Schedule E behind a $336/year paywall. If you have 1-10 units and just need expense tracking and tax prep, here's why Stoopkeep is the smarter choice.
The Bottom Line Up Front
Stessa is a genuinely capable platform. If you're an active real estate investor building a multi-property portfolio and want acquisition tools, NOI dashboards, and lender-ready reports, it earns its place.
But Stessa has been raising prices. Its full Schedule E tax export—the one feature most independent landlords actually need—is now locked behind the $28/month ($336/year) Pro plan. For a landlord with 3 units who just wants to stop losing receipts, that's a lot of money for features you'll never open.
Stoopkeep was built for exactly that landlord. Simpler. Cheaper. AI-first. Laser-focused on one job: turning your receipts into a finished Schedule E.
How They Compare
| Feature | Stoopkeep | Stessa |
|---|---|---|
| Core Focus | AI receipt tracking & Schedule E | Portfolio management & acquisitions |
| IRS Schedule E Export | ✅ Included in Pro ($99/yr) | ⚠️ Pro plan only ($336/yr) |
| AI Receipt Scanning | ✅ Auto-maps to Schedule E lines | ✅ Available, broader scope |
| Free Plan | Unlimited properties + 20 AI scans | Limited — no tax export |
| Tenant Maintenance Link | ✅ No login required | ⚠️ Paid tier, portal login required |
| Deal Analysis / NOI Dashboard | ❌ Not in scope | ✅ Core feature |
| Annual Cost for Tax Features | $99/year | $336/year |
What Stessa Gets Right
Let's be honest about where Stessa shines:
- Portfolio visibility. Stessa's dashboards give investors a real-time picture of NOI, cash flow, and net worth across their entire portfolio. If you're actively growing and need that 30,000-foot view, it's well-built.
- Deal evaluation. Integration with Roofstock means you can analyze potential acquisitions without leaving the platform.
- Bank-level reporting. Stessa generates lender-ready reports—useful if you're refinancing or applying for new loans.
- Established brand. Stessa has been around for years and has a large, active user community.
These are real strengths. The question is whether you need them.
Where Stessa Falls Short for Small Landlords
The price hike problem. Stessa was beloved when it was essentially free. After its acquisition and subsequent pricing changes, the features that matter most for Schedule E prep are now gated behind its highest tier. Users on forums like BiggerPockets have been vocal about the sting of those increases.
Schedule E is an afterthought. Stessa is built for portfolio investors. The Schedule E export exists, but it's not the center of the product—it's one feature among many, and an expensive one to unlock.
Tenant portal friction. Stessa's maintenance request feature requires tenants to log in to a portal. In practice, most tenants don't bother, and you're back to fielding texts anyway.
Bloat for simple needs. If you have 2 duplexes and want to track receipts and file your taxes, Stessa's acquisition tools, refinancing calculators, and investor dashboards are dead weight you're paying for.
What Stoopkeep Does Instead
Stoopkeep has no portfolio dashboards, no deal analysis, no lender reports. That's intentional.
What it has:
- Snap-and-done receipt capture. Photo → AI extracts vendor, amount, date → auto-categorized to the correct Schedule E line (Repairs, Insurance, Taxes, etc.). Takes 10 seconds.
- "Needs Review" inbox. Every AI categorization surfaces for your approval before it locks in. You stay in control.
- One-click Schedule E CSV. At tax time, export a clean file sorted by property and IRS line item. Hand it to your CPA or import into TurboTax.
- No-login tenant maintenance link. Share a link. Tenant submits a photo and description in 15 seconds—no account, no app download. The cost hits your Schedule E automatically.
- Flat pricing. $99/year covers unlimited properties. It doesn't scale with your unit count.
The Pricing Gap Is Hard to Ignore
| Stoopkeep Pro | Stessa Essential | Stessa Pro | |
|---|---|---|---|
| Annual Cost | $99 | $144 | $336 |
| Schedule E Export | ✅ | ❌ | ✅ |
| AI Receipt Scanning | ✅ | ✅ | ✅ |
To get the Schedule E export from Stessa, you're paying $336/year—3.4× the cost of Stoopkeep Pro. Both plans are deductible on Schedule E Line 8. At a 22% tax rate, Stoopkeep's effective annual cost is about $77.
Who Should Use Which
Stoopkeep is the better fit if:
- You own 1–10 rental units and self-manage.
- Your priority is tracking expenses accurately and filing Schedule E without hassle.
- You've felt the sting of Stessa's price increases and want a focused, affordable alternative.
- You don't need deal-finding tools or portfolio dashboards.
Stessa is the better fit if:
- You're actively acquiring properties and want integrated deal analysis.
- You need lender-ready NOI reports for refinancing.
- You manage a larger portfolio and want a single dashboard for financial performance across all properties.
- The $336/year is justified by the full breadth of features you actually use.
The Honest Summary
Stessa built a great platform for a specific type of user: the growth-minded real estate investor. If that's you, it's worth the cost.
But if you're an independent landlord who fixes things yourself, Zelle-pays contractors, and dreads tax season because receipts are everywhere—Stessa is asking you to pay enterprise prices for features you'll never need.
Stoopkeep is what Stessa used to be: lightweight, focused, and built around the one thing that actually matters at tax time.
Try Stoopkeep free. Scan your first receipt in under a minute and see what a purpose-built tool feels like.