Stessa Bookkeeping Services & Rental Property Accounting

Stessa is free-to-start property management and asset software for rental property owners — it links your bank, credit card and mortgage accounts, auto-imports transactions into a fixed, Schedule E–aligned category list, and produces a tax package your CPA can file from. Since 2021 it has been part of the Roofstock family, and its Cash Management accounts (banking services provided by Thread Bank, Member FDIC) can feed transactions straight into your books.

What Stessa is not, by design, is a full double-entry accounting platform — and it does not sync with QuickBooks. The automation is only as good as the daily decisions made inside it. Maxim Liberty bookkeepers have kept investor books since 2005, working directly inside client Stessa accounts at $15/hour on plans from $75/month.

Stessa Tracks Your Portfolio — Someone Still Has to Keep the Books

Stessa positions itself against generic accounting software for good reason: setup is fast, the reports are real-estate-native (Income Statement, Net Cash Flow, Schedule of Real Estate Owned, Tenant Ledger), and the category list maps directly to IRS Schedule E. But the same design choices that make it simple make it unforgiving. The category list is fixed — Stessa does not support custom categories — imports are one-way, and there is no general ledger underneath to catch what categorization gets wrong.

That means the quality of your books is the quality of your transaction review. Kept current daily, Stessa produces genuinely tax-ready records. Left alone for a quarter, it produces a very organized pile of wrong numbers.

Where Stessa Books Go Wrong

The failures we clean up most often: auto-imported transactions piling up uncategorized until nobody remembers what they were; mortgage payments booked whole instead of split between principal, interest and escrow; transfers between accounts counted as income or expense; security deposits treated as revenue; and capital expenses written off as repairs — which misstates both your P&L and your basis at sale.

Re-linked bank connections quietly duplicating months of transactions is the other classic. Stessa provides split, merge and duplicate tools for all of this — but tools are not judgment, and none of them run themselves.

Core Stessa Bookkeeping Functions We Manage

1. Daily Categorization and Review

Every imported transaction reviewed and coded against Stessa’s Schedule E–aligned master list — income, repairs, professional fees, utilities — so the reports stay true in real time, not just at tax time.

2. Mortgage, Escrow and Transfer Splitting

Loan payments split correctly into principal, interest and escrow; inter-account transfers and owner contributions kept out of income and expense where they don’t belong.

3. CapEx vs. Repairs Discipline

Improvements tracked in Stessa’s Capital Expenses categories rather than expensed as repairs, protecting both your current-year Schedule E and your cost basis when you sell.

4. Account Reconciliation and Duplicate Cleanup

Linked banks, credit cards and Stessa Cash Management accounts tied out regularly; duplicate imports merged, broken connections re-linked, security deposits held as the liabilities they are.

5. Reports and the Year-End Tax Package

Income Statement, Net Cash Flow and Schedule of Real Estate Owned kept accurate through the year, so the tax package your CPA receives needs review — not rework.

The Stessa Rescue: Fixing a Year of Unreviewed Auto-Imports

Most Stessa cleanups start the same way: the imports ran faithfully all year and nobody reviewed them. We work the backlog property by property — categorizing, splitting mortgage and escrow payments, merging duplicates, moving capital work out of repairs — then reconcile each account forward until the portfolio is current and the tax package is filing-ready. Catch-up work is covered by our 100% money-back guarantee on your first deposit.

Why Outsource Your Stessa Bookkeeping to Maxim Liberty?

Stessa’s Portfolio Collaborators feature exists for exactly this: the vendor documents an editor role for letting a bookkeeper manage transactions while you keep owner control. Every Maxim Liberty plan includes a dedicated bookkeeper plus a supervisor who is your single point of contact and quality-checks the work.

• Working inside your Stessa account daily via collaborator access you control
• Categorization, splits, CapEx and reconciliation handled — reports always current
• US-headquartered since 2005; plans from $75/month, $15/hour for businesses
• 100% money-back guarantee on your first deposit

What Our Stessa Clients Say

“I’ve been using Maxim Liberty for my real estate bookkeeping and Stessa software setup/management, and my experience has been outstanding from start to finish.The team is incredibly prompt—responses come quickly, deadlines are met, and they’re always proactive about upcoming tasks or potential issues. …” — Ramsey Sweis