What to ask in a property management software demo
A demo shows the happy path, so use your time on the questions it skips: what it costs at your unit count, how your data gets in and out, which tax reports it produces, how rent reaches your bank and what happens when you leave. Fifteen questions cover it. A clear answer is specific and in writing; a vague one is a signal to ask again.
What should you ask about price?
- What is my monthly bill at exactly my unit count, including any minimum?
- Which fees do tenants pay, and which do I pay?
- Is there any setup, onboarding or data migration charge?
A clear answer is a number. "It depends" without a follow-up is not an answer.
What should you ask about your data?
- How do I get my current tenants and leases in: manual entry or a file import?
- Can I load opening balances and deposits, and how are deposits shown?
- What can I export, in what format, and can I do it myself at any time?
- Who owns the data if I cancel, and how long is it kept?
Ask to watch an import of a messy sheet, not a clean one. Your sheet is not a sample.
What should you ask about books and taxes?
- Is there a separate set of books for each property or LLC?
- Does the product produce a report that maps to Schedule E lines?
- How are 1099-NEC reports handled for vendors, and does the product file them or only list them?
The IRS expects the landlord to report rental income and expenses on Schedule E, so a report that lines up with it saves time at tax season. If the seller says the product does not file something, take that as a plain fact and plan around it.
What should you ask about rent and payments?
- Does rent go straight to my bank account, and how many days does it take?
- What happens on a failed or reversed payment, and what does it cost?
- How are partial payments and late fees applied?
What should you ask about support and leaving?
- How do I reach a person, and what are the support hours?
- Is the agreement monthly or annual, and does it renew by itself?
- What exactly can I take with me if I leave?
Write down the answers during the call and send them back by email the same day with "please confirm". Confirmation in writing is worth more than a good demo.
What answers should make you stop?
Some answers are a reason to pause the sale. None of them is proof the product is bad; they are proof you do not have what you need to decide.
- "We will send pricing after the call" with no number for your unit count.
- "You can export anything" without showing an export on screen.
- A feature shown from a slide, not from the product.
- No clear answer on who owns the data after you cancel.
- A start date that depends on the seller's onboarding queue, with no written date.
Bring a second person if you can. One of you asks the questions and the other writes the answers down, so nothing is lost when the demo moves quickly.
How DoorKeeping handles it
For DoorKeeping the answers are short: $2 per unit per month for everything, no setup or minimum, rent paid straight to your own bank, a separate set of books for each property, and Schedule E and 1099-NEC reports from those books. The 1099-NEC is a report to hand to your preparer; DoorKeeping does not e-file it.
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, About Schedule E (Form 1040), Supplemental Income and Loss, read Oct 30, 2026
Questions
- How long should a software demo take?
- Thirty minutes is enough if you bring the questions. Ask to see your own data go in.
- Should I ask for a written quote?
- Yes. A written quote with the fees you pay and the fees tenants pay avoids surprises on the first invoice.
- What is the most useful question?
- What can I export if I leave? It shows how the company treats your data.