Can my existing data come across, and how long does it take
A running hotel already has a guest list, reservation history, outstanding balances and rate tables. Ask specifically: which data types can be imported, in what format, who does the import work, and how you operate during the transition. An answer along the lines of "just type it in as you go" means the true cost of switching is far higher than the quoted figure.
How do I get my own data back out
This is the most important question and the least asked. If you decide to stop one day, can you export everything in a readable format, or only a handful of printable reports? Operating data belongs to the hotel. A vendor who avoids this question is locking you in with your own data.
What can be adapted to how I work
Every hotel names its room types, splits its shifts and calculates its surcharges differently. Ask what you can change yourself in settings, what requires the vendor, and what is fixed forever. Software that forces a hotel to change its process will be worked around by staff, and the data ends up back in someone's private spreadsheet.
Cloud or a server at the property
Cloud starts quickly with no infrastructure of your own — good for an independent hotel that wants to begin now. A server at the property gives you full custody of the data and keeps working when the outside connection has problems, which usually suits multi-property groups. Neither is right for everyone — but if a vendor offers only one model, you should know that up front.
Who supports me, in what language, at what hours
Hotels run around the clock, and incidents favour nights and holidays. Ask about support channels, hours, and most of all whether the person helping understands hotel operations or is reading from a script. A team that knows the trade will guess what you are facing before you finish describing it.
How long before a new hire can use it
This industry turns staff over constantly. If every new receptionist costs a week of software training, that cost repeats forever. During the demo, have your own staff attempt a real task — checking in a walk-in guest, for instance — instead of watching the salesperson do it.
What is in this price and when does it rise
Ask what is charged per room, what is charged per user, what is a one-off setup or training fee, and how the price moves when you add a property or switch on another module. A quote that cannot tell you what happens as you grow is an incomplete quote.