Hey Jeff, Bob - Geoff was telling me you all had a good autocross last weekend. Sorry I missed it.
I miss having a Porsche over here. I gotta tell you the European style driving is where it's at. Nobody - I mean nobody hogs the fast lane. Speed limits are 70 mph on the motorways, but anything up to 100 is tolerated. Don't get me started on the backroads. Speed limits are 40-50-60 mph, and everybody is polite and road aware. Everybody just wants to keep moving, I've encountered no attitude on the roads at all. I drive like I always did in Canada except instead of getting dozens of tickets and no end of grief, I fit right in. There's no intersections. It's all done with roundabouts and if no one is coming you don't even have to slow down! 60 mph, apex the round bit, and carry on! I honestly don't know if I can ever go back!
Anyway - to the OP...on the topic of 996 maintenance. I did what little was required by myself. Oil changes were a ten minute job and I didn't even have to jack the car up, although it did make it easer. Brakes were easy, as they normally are. Transmission fluid swap - easy. The toughest job I had to do was replace a coolant tank. I had to do partial engine drop, but even with that it was done in about three hours. It was a pain, BUT oh so much esier than replacing the fuel line in my friend Marcus' 1988 Carera clubsport. That took five days and required removal of the intake manifold up!
It kills me when people say you can't DIY a 996...what the hell is that about? Absolute total utter rubbish! It's a car! Just what kind of DIY are you planning on doing? I guess if you had to set up the valve train then the 996 might be more difficult but really..is that aDIY job? (I know it is for you Jeff, but I gotta draw the line somewhere).
On balance I'd have to say the 996 was much easier to maintain than my 911, which needed endless little things done to it. The 996 just worked didn't it...the job list was very short, and the jobs easy.
I have limited experience with the 964 and none with the 993, but those two are probably the most complex ones of all. I understand the 993 has two oil filters, and one of them is located underneath and up in the engine so is very difficult to reach. Uughh.
rant off
Good luck with your choice. I ran both kids in the back of my 996 all the time. I loved it, they loved it. Perfect family car.