Hey in_burrito, I own a 99 996 c2 coupe and have had it for almost 2 years. This is the second Porsche I've owned.
You are correct about the 993 pricing, it's partly a 'purist' issue and partly just simple economics. They made a lot more 996's than they did 993's.
IMO the 996 is a much better daily driver, it's faster, handles better and is the first 911 that was lighter than its predecessor. It's much easier to drive fast than the 993. Plus the A/C works a helluva lot better.
Both have their share of weaknesses and the best place to go for info is
Rennlist or some of the links from there.
Major watch-outs are:
993- valve guides and clogged air injection porst, this can be expensive if it cooks the engine
996- oil leak from RMS (~$800 to get fixed),
Porsche ownership for me is a love/hate thing. There are a lot of chintzy little bullshit things that break on the car that add up.
It's also not an inexpensive car to own. Mine's a daily driver (~12000 mi/yr) and I'd estimate it costs about $2000/year in maintenance and depreciation. In particular rear tires wear VERY QUICKLY and are very expensive, plus you can't rotate tires on the car so you're screwed there.
Personally I'd talk most people out of buying a Porsche, I knew ahead of time that it wasn't a rationale decision but after much internal and external debate I bought it over an M3 that I was also looking at.
It's a lot of fun to drive but there are much better values in sports cars out there.
On the good side it gets decent mileage both in town (~21) and on the interstate (27), oil changes only once every 10,000 miles but it takes 10 quarts of Mobil 1.
Where are you located in Florida?
ETA: here's something you should really read before looking/purchasing
PPIIn Largo I recommend Joe Vatter at
Germantech for any work you need done, he's an EXCELLENT independent Porsche shop.