In order:
I already am a DM in another group, and hope to take over a second group eventually, but the Friday games I'll never touch. The players are too "out there", and they actually accept that DM's ways, even if they do complain about as much as I do at times. Especially when he's cheap, or keeps bringing things back from the dead when Resurrection and such don't exist (although he's bringing back a "form" of Reincarnation so that's good at least).
The group always has a DM run NPC. The stuff the DM does to that poor bastard is ridiculous.
Pun-Pun will not exist in his world. Why? Because if you pull off something broken, and he realizes it (and he will), you will be slammed down hard and nerfed faster than you can shake a stick. If a lvl 20 Wizard makes him laugh, a Pun-Pun will only make that evil laugh louder when he abolishes it.
I will NEVER meet the prereqs for a Savant. There's just no way. I've looked at it, and I'm not into that kind of thing regardless. That being said, he'd like nothing more than for me to go Illithid for 7 levels (Savage Species) and then take that PrC because that would be "perfect" for him. I'd really rather not play into his hands. I know for a fact that he doesn't see what I'm doing because when I bring up Swashbuckler, he thinks I'm referring to the Pathfinder version, which he hasn't accepted/denied yet. The reason I chose what I did was simply because of the fact that I'm pretty sure that I'll only get maybe six class levels in there due to all the LAs. One suggestion was go monk and take Kung-Fu Genius. The only problem is the lack of stacking, and I have yet to meet a single person who's in favour of the monk at all. That being said, I couldn't really see a worse class to take with that many LAs. Aside from that, the DM really wants me to go psionic. The only one I can even remotely consider is the Lurker, but even that's pushing it.
I wouldn't say I have the finest stories. Just the most out there to date. Someday we'll meet someone worse, I'm sure.