What is important questions when evaluating Software Systems?

Im currently working with analyzing and evaluating systems like customer portals, sales systems, CRM etc. Now i got the task to put together a common template we can use when evaluating these. I have searched through some research but they are really dry and not giving me any good input. Therefor i would like to ask people with experience:

What is the most important questions when evaluating systems?

Is there any known practices or templates i should use or avoid?

Is there any "new" or modern ways of analyzing and evaluating software?

Would be awesome with some input.