The major issue with being a mod is when forum members you actually like misbehave and you have to ask them to stop, which comes across as authoritative no matter what, or take some kind of moderator action against them. You don't have the option of being nice to them simply because you like them because they're still doing something they shouldn't and your job is to deal with that, regardless of who it is.
Makes you feel kinda bad sometimes.
Also the issue of being totally unsure of if you were justified in doing something sometimes, which I know Bubba has had to deal with. It's a bit more of a problem on this forum since we're specifically against moderating something based upon personal opinion but all moderator actions come down to personal opinion to some degree.
Also it's appreciated that you made a separate thread for the derail.