Cloud based maintenance management software is now the default rather than a choice, which makes the interesting question narrower than it used to be. Almost nothing about maintenance management is different in the cloud: the register, the schedule, the work order and the history are the same four things. Two practical matters do change, and they are the ones worth attention before signing. The first is that the system is reachable from the machine, which is where it needs to be. The second is that your history now lives on somebody else's disk, which makes the export a contractual question rather than a technical one.
What genuinely improves: reach
A technician at a machine can raise a job on a phone, and a supervisor can see what is overdue from anywhere. That is the whole practical gain and it is a large one, because it is what makes records get written at the time rather than reconstructed later.
What genuinely improves: nobody patches a server
A small maintenance team should not also be running a database, and self-hosted maintenance systems have a well-earned reputation for being three versions behind because nobody had time. This is a real cost that quietly disappears.
What to ask about: offline
Plant rooms, basements, yards and cold stores have no signal, and that is exactly where equipment is. Ask to raise a job in airplane mode during the demo. A product that silently loses it will be blamed for missing history it caused.
What to ask about: getting your data out
Ask for a full export of assets, schedules, work orders and history, in a format you can read, available to you without asking. If that is a support ticket rather than a button, your history is hostage, and a maintenance history is worth more the older it gets.
Questions people ask about cloud based maintenance management software
Is cloud less secure for maintenance data?
Generally the opposite, for a small team: a vendor patches continuously and an unloved on-premises server does not. What changes is that access control becomes somebody's job rather than nobody's.
What happens if the internet goes down?
The work still happens; the recording waits. This is why offline capability on the mobile app matters more than uptime on the web app.
Can we self-host instead?
Some products allow it and it makes sense where a site genuinely has no connectivity or a hard policy. Budget for the patching and the backups, because those are the costs the cloud was absorbing.