How to Switch from Stessa to TallyRoost

Who this migration guide is for

You use or are winding down Stessa and want owner rental books in TallyRoost: per-property income and expenses, Schedule E–oriented categories, and export totals for your CPA. TallyRoost is not property management software — it is owner P&L and bookkeeping handoffs only.

Still comparing products? Read TallyRoost vs Stessa first. This page is the how-to once you plan to move.

Fair reasons owners leave Stessa (not a hit piece)

Stessa works for many landlords — especially when their CPA is already happy with Stessa reports. Common reasons owners consider a switch are about fit, not failure:

• You want short-term rental books from an Airbnb, VRBO, or Hospitable CSV (upload or paste), not re-keying payouts after a generic dashboard export.
• You want Schedule E–friendly categories and exports as the default owner view — see Airbnb expense categories on Schedule E.
• You prefer plain-English owner cash flow / P&L for a small portfolio without PM-firm workflows (TallyRoost does not offer PM features).

Staying on Stessa is reasonable when your current exports already satisfy your CPA and you rarely touch STR channel detail. No vendor is “wrong” — match the tool to how you operate.

Step 1 — Export from Stessa

1. Choose the date range your CPA will reconcile (often calendar YTD or through your last closed month in Stessa).
2. Download property-level income and expense reports (CSV or PDF — whatever Stessa offers on your plan). Keep raw files for the transition year.
3. Save attachments your preparer still needs (leases, insurance, major invoices) if Stessa stored them.
4. Note what Stessa already counted as income for the year so you do not import the same payouts twice in a new system.

Stessa's export buttons change — use their help center for the current path. We do not document their UI here.

Step 2 — Map operating expenses in TallyRoost

Start with expenses: cleaning, supplies, utilities, insurance, repairs, management, and other recurring costs with consistent per-property labels your CPA can map to Schedule E lines 5–19. Capital assets and depreciation schedules usually stay with your CPA's Form 4562 work — TallyRoost focuses on operating books and export totals, not inventing basis or tax results.

Use the Schedule E expense guide while you clean categories — it is educational, not a filing checklist.

Step 3 — Do not double-count revenue

The most common migration mistake is importing gross rent twice — once from Stessa closing reports and again from channel imports.

Preferred forward path: upload or paste one channel file (an Airbnb earnings CSV, a VRBO payout CSV, or a Hospitable reservations export) so payout totals match one source of truth. If Stessa already holds correct YTD income for the year, many owners leave revenue alone in the new app and only forward new activity — but that is a CPA decision, not our default.

Pair Stessa closing exports with TallyRoost exports for any overlap month so line 3 rent is not duplicated on the return.

CSV upload or paste (what works today)

• Hospitable — reservations export via Legacy exports → Reservations & Financials. Hospitable emails the CSV. Upload or paste that file. Hospitable API reconnect is coming later. Live sync is not available yet.
• Airbnb and VRBO — Airbnb earnings CSV (Create report, not the PDF) and VRBO payout CSV (payout summary). Same Import screen: upload the file or paste it with the header row.
• TallyRoost template — a filled file with a header row and at least one stay.

Steps: How to export booking CSVs · What to paste (and what not to).

TallyRoost does not offer bank connections. If Stessa was your only aggregation layer, plan a channel CSV — we do not claim a bank feed feature.

Step 4 — Schedule E export for your CPA

When categories are stable, run TallyRoost's Schedule E–friendly export totals by property. That file is a bookkeeping handoff: your CPA maps lines 5–19, handles depreciation separately, and files the return. Attach Stessa closing reports for any months still tied to the old system.

Exports are not tax advice and not a filing product — no guaranteed refund or loss outcome.

Run parallel, then cut over

You do not need to cancel Stessa on day one. Export from Stessa, import expenses (and forward stays via CSV upload or paste when ready), compare owner P&L for a closing cycle or two, then close Stessa access when your CPA is comfortable with the transition year.