When to switch landlord software: which month, which day, and what to check first

Why a month end?

On the last day of a month your balances are settled: rent is in, late fees are posted and bank statements close. That gives you one number per tenant to carry over, and one bank balance to check against your books. A switch in the middle of a month means splitting a payment cycle across two systems.

• Rent is normally due on the 1st, so cut over the day before and have tenants pay the new way from the 1st.
• Reconcile the old books to the bank statement before you export.
• Post late fees and deposits through the cutover date so balances are final.

Which dates should you avoid?

Three times of year make a switch harder.

The renewal date matters more than most owners expect. Yardi Breeze's published terms, read on 2026-10-30, describe a one-year agreement that renews automatically, and annual billing is common elsewhere. Look up your own renewal date first and cut over comfortably before it.

How long should the two systems overlap?

Keep the old system readable for one full rent cycle after you cut over. Do not keep updating it; that is how two systems end up disagreeing. If the old product bills monthly, you can cancel after the first cycle. If it bills annually, set the cancellation for before the renewal date and keep your exports.

Example a made-up owner cuts over on June 30 and collects the first rent in the new system on July 1. The old system stays readable through August 1, the owner checks July balances against the bank statement on August 1, and cancels on August 2. If the old plan renewed on July 15, the owner should have given notice before that date, so the plan ends on time.

What does the timeline look like?

1. Six weeks before: test the new product with two real units.
2. Four weeks before: export everything from the old system.
3. Two weeks before: clean the data and load a trial import.
4. One week before: tell tenants the date and how to pay.
5. Cutover day: last day of the month; import opening balances.
6. First rent day: match payments by hand against the bank.
7. Next month end: reconcile, then cancel the old product.

What should you tell tenants?

Tell tenants the date, exactly how to pay from then on, and that the lease does not change. Send the message about two weeks ahead and a reminder a few days before the first rent date. Say what is the same, such as the amount and the due date, before you say what is different.

If tenants had autopay set up in the old system, tell them it ends on the cutover date and they need to set up the new way. Watch the first rent day closely, and match each early payment by hand against the bank.

How DoorKeeping handles it

The import takes current leases and opening balances as of your cutover date, so a month-end cutover leaves nothing to reconcile mid-cycle.

DoorKeeping costs $2 per unit per month with every feature included, no setup cost and no minimum. You import a rent roll from a CSV or XLSX file, and each property gets its own books. Tenants pay your own bank directly, and anything involving money waits for your one-tap approval.

Sources

1. IRS, About Form 1099-NEC, Nonemployee Compensation, read Oct 30, 2026
2. Yardi Breeze, Pricing, read Oct 30, 2026
3. IRS, How long should I keep records?, read Oct 30, 2026

Questions

Can I switch software in the middle of the month?

You can, but a month end is cleaner because balances are final and the bank statement closes.

Should I switch at the start of the year?

Some owners wait until February, after year-end reports and 1099 deadlines are done.

How long should I keep the old system?

Keep it readable for one full rent cycle and keep your exported files for your records.