I love my 944. It's an '88 with about 37k miles on it. It consistantly out handles the 911's on our local pca road trips thru the foothills and keeps up with the boxters easily. It's definately not as quick as a 911 or boxter but it handles like a dream and is a very comfortable car. The engine is in front but the transaxle sits right over the rear wheels so it has perfect 50/50 weight ratio.
There are 2 generations of 944's; pre 85.5 and post. The later cars have a more modern interier. In fact, most people think my car is new. The primary maintenance issue is the timing belt. It needs to be changed every 30k miles. If it breaks, it can do serious engine damage as this is an "interferance" engine - meaning no valve clearance due to high compression. The belt requires a specialized tool to change so if you don't have this tool, it's about a $1200 repair at a good shop.
You could also get a 968. It's basically the same car with suspension improvements and a much more powerful engine (without the turbo issues). Of course, some people don't like the 968 styling where they rounded everything.
Here's mine
