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There are alot of things in the "wiki world" that really aren't very big deals.
Some of these come up often, some come up less often. Some of them are more big deals then others, but still not very big deals.
Take for example a new group or feature on a Wikipedia project. Most of these features really aren't big deals at all. When I come across a request for one there is really one important thing I think about: Why Not? Can I think of any reason that it would hurt to implement the request? If I can't I look at the reason for the request: Does it at the very least make sense? If it does then I vote yes, even if I really don't think it's necessary. Why? Why not?
How about a Request for Adminship: Here again it really isn't a big deal. I will however admit that I generally want to look for a couple things first:
Contributions really aren't a huge deal to me, though a lack of them can make it hard for me to figure out the above. After everything above it still comes back down to Why Not? If they meet the general guidelines then sure go ahead. It is VERY easy for me to agree to take them away if you mess up or go inactive (it makes NO sense to keep people as sysops for years when they never come around anymore :) ). There really isn't anything a normal admin can do which can't be totally undone with a little time by other admins/stewards if they go berserk, I won't vote to promote them if I THINK they're going to go berserk but if I can't find a reason they would (and I think I have enough info to make that decision) then the benefit outweighs that risk.
For most other user requests there is very little to think about and it tends to come down very much to a Why Not? mode of though. Ok they want rollback? Why Not? If I can't see any reason to say they would "fuck up" with them then why not, they can just as easily be taken away. This would hold similarly with something like WP:Importers, the Confirmed group on wikis that have it etc. If you can give an ok reason to have it the only question is Why Not?.
If you were directed here in the midst of a discussion about something else that's doesn't fit above it is because I or whoever linked you thinks Why Not applies. If your here stop and think about it for a second..... there are a lot of discussions that happen on wiki where the final result doesn't REALLY matter in the end. If we say yes what are the chances that something bad will happen? Why Not do it? Are we just delaying the inevitable? What will happen if we DO do it? There is a good chance it won't really matter either way, but still Why Not?
There are some things that Why Not is NOT meant for, at least by itself. These include anything where there is a serious possibility that the individual could do something that would be impossible or very hard to revert, or that could seriously harm the privacy of a user. This specifically includes anything where the Rfx Requester would have to identify to the WikiMedia Foundation for. I.E Oversight or checkuser. A big part of all the WMF projects is trying to have as much public information as possible. To that end we try to delete as much as possible and keep as much transparency as possible.