I'm a sometimes frequent flyer but less often in the US, so I don't have any kind of pre-screening. I have never had a problem, other than the occasional line, with TSA. I actually have found them regularly polite and joking. I think this could be because I'm familiar with the procedures, and generally very well organized to go through screening.
There are lots of horror stories about flying, things can go wrong occasionally, personally I would fly anywhere that's > 3 hours or roughly the break even to get there faster, unless I need a car for some reason. If you are familiar with it it's really not as bad as the horror stories.