Questions to ask during a property-software demo

How to run the demo so the answers mean something

Before the topic-by-topic questions, set the rules of engagement. Ask the vendor to use a sandbox or sample dataset that resembles your portfolio — a few schemes or buildings, a mix of arrears, a maintenance job in progress — rather than a curated demo file. Real-shaped data exposes edge cases that a scripted walkthrough hides.

Invite the people who will actually use the system: a bookkeeper for trust accounting, a portfolio manager for collections, and a trustee or director if schemes are involved. Each will probe a different weakness. Where you cannot judge an answer, ask the vendor to show it rather than describe it.

Keep a simple scorecard. For every question, note whether the answer was demonstrated, described, or deferred to a roadmap. A pattern of deferrals is itself the finding.

• Ask: "Can we use sample data that looks like ours rather than your demo file?"
• Ask: "Show me, don't tell me" whenever a capability is claimed.
• Note which answers are live, which are verbal, and which are "coming soon."

Trust accounting questions

For managing and rental agents this is the area where mistakes become regulatory and financial exposure. The Property Practitioners Act (Act 22 of 2019) sets expectations around trust accounting for practitioners who hold client money, and the system should be designed to support — not undermine — those obligations. Ask how client and business money are kept separate, and have the vendor show it on screen.

Push on reconciliation specifically. Ask to see a bank reconciliation performed in the demo, how unallocated receipts are handled, and whether the ledger can ever be edited in a way that breaks the audit trail. A credible answer shows an immutable or fully logged transaction history and a reconciliation that ties to the cent.

• "How does the system keep trust money separate from agency operating funds?"
• "Show me a live bank reconciliation and how an unallocated receipt is resolved."
• "Can a posted transaction be deleted, and if so, what audit record remains?"
• "What financial reports support an annual audit, and can you export them now?"
• Good answer: separation is structural, the audit trail is tamper-evident, and reports are generated live, not promised.

Tenant screening and collections questions

Screening touches both risk and privacy. Ask which credit and tenant-history data sources the platform draws on, how a prospective tenant's consent is captured, and how screening results are stored and for how long. The Rental Housing Act (Act 50 of 1999) frames the landlord-tenant relationship, and any screening must sit comfortably alongside POPIA consent obligations.

On collections, focus on arrears workflow. Ask how the system tracks who owes what, what reminders and escalation steps it automates, and whether it produces the documentation you would need if a matter proceeds further. A good answer shows an arrears ageing view, a configurable reminder sequence, and a clear record of every notice sent.

• "What screening data sources do you use, and how is tenant consent recorded?"
• "How long is screening data retained, and who can see it?"
• "Show me the arrears ageing report and how an overdue account is escalated."
• "What proof-of-communication record exists for reminders and notices?"

Schemes, levies and CSOS compliance questions

For community schemes the demo must speak the language of sectional title and HOAs. The Sectional Titles Schemes Management Act (STSMA, Act 8 of 2011) and the CSOS Act (Act 9 of 2011) shape how schemes are run, how budgets and levies work, and the oversight role of the Community Schemes Ombud Service. Ask how the levy roll is maintained, how the administrative and reserve funds are tracked separately, and how the system supports the CSOS levy and submissions a managing agent typically has to handle.

Ask to see a levy run end to end: raising levies against units, applying interest on arrears, and producing owner statements. For governance, ask how the platform supports AGM and trustee or director workflows, meeting documentation and a trustee or owner portal. A strong answer distinguishes administrative from reserve fund money clearly and produces scheme-level financials a trustee could actually present.

• "Show me a full levy run, including arrears interest and owner statements."
• "How are the administrative fund and reserve fund tracked separately?"
• "What does the system do to support CSOS submissions and levies?"
• "How does it handle AGM preparation, trustee access and the owner portal?"

Maintenance and inspections questions

Maintenance is where service quality and cost control meet. Ask how a job moves from a tenant or owner logging it, through assigning a contractor, to approval and payment — and whether owners and trustees get visibility along the way. The useful test is whether the workflow reduces phone calls rather than adding admin.

Ask about inspections too: move-in and move-out records, scheduled property condition checks, and whether photos and notes attach to a property and a job. A good answer shows the full chain in the demo, with an audit trail of who approved what and a clear spend record per property or scheme.

• "Walk me through a maintenance job from log to contractor to payment."
• "Can owners or trustees see job status without phoning the office?"
• "How are inspection photos and condition reports captured and stored?"

Compliance, POPIA and data ownership questions

POPIA governs how you handle the personal information of tenants, owners and contractors, and the software is a custodian of much of that data. Ask where data is hosted and in which region, how access is controlled by role, and how the vendor would support you in responding to a data subject request or a breach. A vendor that treats POPIA as a checkbox should worry you more than one that talks about it concretely.

Data ownership is the question most buyers forget. Ask plainly: "If we leave, can we export all of our data, in what format, how quickly, and at what cost?" A confident answer offers a clean, structured export you genuinely own. Evasiveness here, or talk of export fees and proprietary formats, is a long-term lock-in risk.

• "Where is our data hosted, and is it kept in South Africa?"
• "How is access controlled by role, and is access logged?"
• "How do you support us with a POPIA data subject request or a breach?"
• "Can we export all our data on exit — what format, how fast, what cost?"

Migration, support and pricing questions

Migration is where good intentions die. Ask exactly what the vendor migrates for you versus what your team must do, how opening balances and trust account positions are brought across and reconciled, and how long the process typically takes. Get the scope in writing. A vague "we'll help you import" is not a plan.

On support, ask for response-time expectations, the channels available, whether you get a named contact during onboarding, and what training is included. On pricing, get total cost in writing: what is included, what is an add-on, how billing scales as your portfolio grows, and whether there are setup or migration fees. The goal is no surprises after signature.

• "What exactly do you migrate, and what is left to us?"
• "How are opening balances and trust positions migrated and reconciled?"
• "What are your support response times, channels and onboarding training?"
• "What is the all-in price, what scales with growth, and are there setup fees?"