ClaryBook vs Stessa for Landlords: Real Bookkeeping vs a Property Dashboard (2026)

Stessa is one of the most popular tools for landlords who want to track rental property finances. It's free, it connects to your bank, and it gives you a clean dashboard showing income, expenses, and cash flow per property. For a lot of landlords, Stessa is the first tool they try after outgrowing spreadsheets.

But there's a distinction that matters at tax time: Stessa is a financial dashboard, not a bookkeeping system. It tracks your money. It does not keep your books. When your CPA asks for your financials, Stessa's output is not something they can use directly — they'll need to redo the accounting in their own software.

ClaryBook is a bookkeeping tool. It produces the double-entry books, depreciation schedules, mileage logs, receipt documentation, and Schedule E reports that your CPA needs. This is an honest comparison of two tools that look similar on the surface but solve fundamentally different problems.

What is Stessa?

Stessa was founded as a free financial tracking tool for residential landlords. You connect your bank accounts, transactions categorize automatically, and you get a dashboard showing per-property cash flow, income, expenses, and portfolio performance.

In 2022, Roofstock — a real estate investment marketplace — acquired Stessa. Since then, a Pro tier ($20/month) was introduced, some features moved behind the paywall, and the product has increasingly served as a funnel for Roofstock's property buying and selling marketplace.

The free tier remains functional: unlimited properties, bank connections, automated transaction categorization, per-property income/expense tracking, and basic financial reports (income statement, net cash flow).

The dashboard vs bookkeeping distinction

This is the single most important difference between the two products, and it affects everything downstream.

A financial dashboard shows you where your money went. You see income, expenses, and net cash flow. You can filter by property. You get charts. It's useful for monitoring your portfolio.

A bookkeeping system maintains proper accounting records: double-entry journal entries, a chart of accounts, a trial balance, a balance sheet. It produces the financial statements that the IRS and your CPA expect. It tracks depreciation as journal entries, not just numbers on a screen. It stores receipt documentation linked to transactions. It generates a complete tax package.

Stessa is the first type. ClaryBook is the second. Both are useful — but they serve different purposes. If your CPA has ever told you "I need your books, not a screenshot of a dashboard," you know the difference.

Feature-by-feature comparison

Transaction tracking

Stessa: Connects to bank accounts and auto-imports transactions. Rule-based categorization. When Stessa sees "$347.89 at Home Depot," it categorizes it based on the vendor name using rules you've configured or it has learned from your previous categorizations.

ClaryBook: Two input paths. (1) Send a receipt photo or describe the expense in plain language via Telegram, the web app, or the iOS app — AI categorizes it with context awareness. (2) Import bank transactions via CSV and auto-match them with existing records. ClaryBook stores receipt images linked to every transaction.

Receipt management

Stessa: No receipt scanning. No receipt storage on the free tier. Pro tier ($20/month) has basic document storage but no OCR or AI extraction. If the IRS asks for documentation of a transaction, you need the original receipt from somewhere else.

ClaryBook: AI-powered receipt scanning. Send a photo and ClaryBook extracts vendor, amount, date, and line items, then categorizes the expense. Receipt images are stored permanently and linked to the transaction. Searchable document management with full-text search.

Depreciation

Stessa: No depreciation schedules. Stessa records property values but does not calculate monthly depreciation, generate depreciation journal entries, or track cost basis over time. For most landlords, depreciation is the single largest annual deduction — a $300,000 residential property generates about $10,900/year over 27.5 years. Stessa leaves this entirely to you or your CPA.

ClaryBook: Full depreciation schedules with cost basis, placed-in-service date, and useful life. Monthly auto-journal entries post the depreciation expense automatically. Feeds into per-property P&L and tax deduction totals.

Double-entry accounting

Stessa: No double-entry accounting. Simplified cash-basis tracking. No chart of accounts, no journal entries, no trial balance, no balance sheet. This is the fundamental reason CPAs can't use Stessa data directly — it's not proper books.

ClaryBook: Full double-entry system. Chart of accounts, journal entries, trial balance, income statement, balance sheet, and cash flow reports.

Mileage tracking

Stessa: None. No mileage tracking of any kind.

ClaryBook: IRS-compliant mileage log. Text "drove 22 miles to the property for an inspection" and it's recorded with date, distance, purpose, and deduction calculation at the current IRS rate ($0.725/mile for 2026).

Material participation hours

Stessa: None.

ClaryBook: Track hours toward the IRS 500-hour material participation threshold (Form 8582). Log via chat: "spent 3 hours painting and cleaning unit 2." This determines whether your rental losses are passive or active — worth thousands in tax treatment.

Invoicing

Stessa: None. No invoicing capability.

ClaryBook: Branded PDF invoices, recurring invoice templates, payment tracking, A/R aging, overdue reminders, credit notes.

Contractor tracking

Stessa: Basic expense tagging by vendor. No 1099-NEC tracking or threshold alerts.

ClaryBook: 1099-NEC contractor management with $600 threshold alerts. Track payments to every plumber, electrician, and handyman across properties.

Loan and mortgage tracking

Stessa: No amortization schedules. No principal/interest split tracking.

ClaryBook: Loan/mortgage tracking with amortization schedules. Automatic principal/interest split journal entries for each payment.

Schedule E and tax package

Stessa: Schedule E-aligned categorization on the dashboard. Exports a basic tax report. But without depreciation, mileage, hours, or receipt documentation included, the CPA still needs to supplement the Stessa data significantly.

ClaryBook: Full Schedule E Part I mapping (Lines 3-19) per property. Depreciation, mileage deductions, and material participation data all included. CPA tax package export bundles everything — P&L, Schedule E, receipts, depreciation schedules, mileage log — into one download.

Where Stessa is better (honest assessment)

Stessa has real advantages that ClaryBook doesn't match. Here's where it wins:

Free tier with bank feeds. Stessa Essential is genuinely free with unlimited properties and direct bank connections. ClaryBook costs $30/month after a 30-day trial and uses CSV import (not live bank feeds). If basic expense tracking is all you need and price is the main factor, Stessa's free tier is hard to beat.

Live bank connections. Stessa connects directly to your bank accounts via Plaid. Transactions sync automatically. ClaryBook currently requires CSV import for bank reconciliation — functional, but more manual.

Portfolio analytics. Stessa Pro offers cap rate calculations, rent estimate comparables (powered by Roofstock data), portfolio benchmarking, and property value tracking. ClaryBook calculates NOI but doesn't have market comp analysis or property valuation tools.

Android app. Stessa has both iOS and Android. ClaryBook has an iOS app and web app, but no Android app. (Android users can use ClaryBook via the web app or Telegram bot.)

Larger landlord community. More landlords know Stessa. There are more YouTube tutorials, Reddit discussions, and BiggerPockets threads about it. ClaryBook is newer and less established.

Where ClaryBook is better

ClaryBook's advantages are about accounting depth — the difference between tracking money and keeping books:

• Double-entry accounting — chart of accounts, journal entries, trial balance, balance sheet (Stessa has none)
• Depreciation schedules — automatic monthly journal entries with cost basis tracking (Stessa has none)
• AI receipt scanning — photo-to-categorized-expense with receipt storage (Stessa has no receipt scanning)
• Mileage tracking — IRS-compliant log with deduction calculation (Stessa has none)
• Material participation hours — 500-hour threshold tracking for Form 8582 (Stessa has none)
• Invoicing — branded PDFs, recurring templates, A/R aging, credit notes (Stessa has none)
• 1099 contractor tracking — $600 threshold alerts (Stessa has basic tagging)
• Loan/mortgage amortization — principal/interest split journals (Stessa has none)
• Conversational AI — log expenses by text message, no dashboard navigation
• Complete CPA tax package — one export with everything your CPA needs
• Document management — OCR, expiration tracking, full-text search for leases, insurance, inspection reports
• No data harvesting concerns — ClaryBook is a bookkeeping tool, not a real estate marketplace mining your financial data for investment intelligence

The Roofstock question

Since Roofstock acquired Stessa in 2022, the product's direction has shifted. Features moved behind the Pro paywall. Development has slowed. And the product increasingly promotes Roofstock's real estate marketplace — property buying, selling, and 1031 exchanges.

Some users on Reddit and BiggerPockets have expressed concern about data privacy: Roofstock is a real estate investment marketplace, and your property financial data (rents, expenses, cash flow, property addresses) is valuable market intelligence. Whether Roofstock uses this data for marketplace purposes is a question each landlord should consider.

ClaryBook is a bookkeeping product. It doesn't operate a real estate marketplace, doesn't use your financial data for investment analysis, and has no secondary revenue stream that depends on your property data.

Who should use Stessa?

Stessa is a reasonable choice if:

• You want free basic expense tracking with bank feeds
• You primarily want a portfolio dashboard — income, expenses, cash flow per property
• Your CPA is comfortable doing the accounting from a transaction list
• You don't need depreciation tracking, mileage logs, or receipt scanning
• You're interested in portfolio analytics (cap rates, rent estimates, benchmarking)
• Price is the primary factor ($0 vs. $30/month)

Who should use ClaryBook?

ClaryBook is the better choice if:

• You want your CPA to receive complete, ready-to-use books at tax time
• You need depreciation schedules tracked automatically
• You want receipt documentation stored and linked to every expense
• You need mileage and material participation tracking for IRS compliance
• You want real double-entry accounting — balance sheet, trial balance, journal entries
• You need invoicing for tenants or contractors
• You want to track 1099 contractor payments with $600 threshold alerts
• You prefer logging expenses by text message instead of navigating an app
• You want a complete Schedule E tax package in one download

The bottom line

Stessa and ClaryBook serve different purposes. Stessa is a property dashboard — it shows you where your money went, per property, with charts. It's free, it connects to your bank, and it's useful for monitoring your portfolio's financial performance.

But a dashboard is not books. When tax season arrives, your CPA doesn't need a dashboard — they need depreciation schedules, receipt documentation, mileage logs, proper double-entry journals, and a Schedule E that maps to IRS line items. That's bookkeeping. And that's what ClaryBook does.

If all you need is a free way to see income vs. expenses per property, Stessa is fine. If you need your books actually done — CPA-ready, audit-defensible, with every deduction tracked and documented — ClaryBook is the tool built for that.