Where the product's centre of gravity sits
Some property CRMs are built around the telecalling desk and speed of response; others around projects, inventory and booking paperwork. Ask each vendor to show their busiest screen. Whichever screen they open first tells you what the product was really designed to do.
Team size the product assumes
A four-person brokerage and a thirty-person developer sales team stress very different parts of a CRM. Ask about assignment rules, multiple pipelines, manager dashboards and permissions, and request a reference customer at your scale.
Breadth versus depth
Vertical products trade general capability for property-specific workflow. Judge how much of your daily work is truly property specific. If most of it is enquiry handling, calling and follow-up, general sales capability may matter more than the specialised modules in the brochure.
Implementation effort and support
Ask what onboarding includes, how long it takes, who supports you afterwards and what response commitments exist in writing. With smaller vendors this is often the difference between a rollout that lands and one that stalls in week three.
Channel coverage and data portability
Test how portal leads arrive, how calls and WhatsApp are recorded, and how cleanly your data exports. Run the export during the trial, not at the end of a contract, because that is the single most useful thing you can learn about any vendor.