How to test landlord software in a free trial with your own data
Load two real units, post one real payment, run the one report you need most and try the export before the trial ends. A demo account hides the problems that matter, such as messy tenant names, partial payments and deposits. Two hours with real data tells you more than a week of clicking through sample screens.
What should you prepare before you start?
Pick a short list of tasks that you do every month, and write down what a good result looks like. Without that list, a trial turns into browsing.
- Choose two units, ideally one with a clean history and one with a messy one (a partial payment, a deposit, a late fee).
- Gather the lease, the tenant's contact details and the last three months of payments for those units.
- Write down your current balance for each tenant on the day you start.
- List the three reports you rely on: for example a rent roll, a profit and loss per property and a list of deposits held.
What should you do during the trial?
- Add the property and its owner entity the way you actually hold it, whether one LLC per property or a personal name.
- Add the two units and their tenants and leases. Note how many fields you had to type by hand.
- Record one rent payment that does not match the rent exactly, such as a partial payment, and see how the balance reads.
- Record a deposit and check that it shows as held for the tenant, not as income.
- Run your three reports and compare each total with your own numbers.
- Connect a bank feed if the product offers it, and see whether a deposit matches the right tenant.
- Try to export a tenant ledger and a report to a file you can open.
Do not skip the export. It is the only test that tells you how hard leaving will be, and it costs ten minutes.
How do you decide?
Give each product a pass, fail or not sure on every step, and write one sentence on any fail. A fail on balances or deposits matters more than a fail on looks.
| Test | Pass means |
|---|---|
| Add a unit and tenant | Done in minutes, with few retyped fields |
| Partial payment | Balance and history read correctly |
| Deposit | Shown as held, not as income |
| Reports | Totals match your own |
| Export | File opens with the columns you need |
What mistakes do owners make in a trial?
- Testing with sample data, which never contains the messy case.
- Starting a trial so close to month end that you cannot see a full cycle.
- Forgetting the trial end date and landing on a paid, annual plan.
- Sending real tenants a payment link before you have checked the numbers.
Set a calendar reminder for two days before the trial ends so the decision is yours, not the billing system's. Keep your own records alive in your current system until you cut over.
What should you do when the trial ends?
Decide on the date, not on the invoice. If the product passed, pick a cutover at the next month end and note what you will load: current leases, balances and deposits, not years of history. If it failed, export what you entered, cancel in writing and keep the confirmation.
Either way, write three lines for yourself: what worked, what did not, and what you would ask the seller. Two weeks later those notes are the only record of why you chose what you chose.
- Cancel any trial you will not keep before the billing date, and save the confirmation email.
- Tell nobody outside your household about the new system until balances match.
- Keep your old records unchanged until the new system has run one full rent cycle.
How DoorKeeping handles it
You can try DoorKeeping the same way: import a rent roll for two properties as a CSV or XLSX file, check the units, tenants and leases it reads, then ask your Claude or ChatGPT for the balances you wrote down and compare them with your own.
DoorKeeping costs $2 per unit per month with every feature included, no setup cost and no minimum. Tenants pay your own bank by bank transfer, which is always free, or by card with a 3% card fee, which covers card processing. DoorKeeping never holds your rent, and anything involving money waits for your one-tap approval.
Sources
- IRS, How long should I keep records?, read Oct 30, 2026
Questions
- How many units should I use in a software trial?
- Two is enough: one clean and one messy. More just adds typing without teaching you more.
- Should I send tenants a payment link during a trial?
- Not until you have checked balances and deposits. Test with your own payment first.
- What should I keep from the trial?
- Your own records. Keep the old system or sheets running until you cut over.