I go in and look at what features are offered in the software solution, then I look at their forums and user community.
For example, vBulletin requires you have a license to register on their support community, and to download mods; so they would be no use to me as my members/staff would be unable to post requests there for assistance or mods, etc.
UBB however allows anyone to register, has a pristine support community, friendly atmosphere, etc; so that's how I ended up with my decision way back when...