Write down a typical and an awkward booking
Include a normal reservation and a case involving an exception, different audience, recurring time, or combined space. Ask each vendor to show both from setup to confirmation.
Check operational fit
Review access rules, advance windows, cancellations, multiple locations, guest booking, and pricing where relevant. Confirm which capabilities are available on the plan you would buy.
Plan the handover
Ask how people, rooms, and existing reservations move into the new system. Decide which old links and booking channels need a redirect or a clear transition date.