Trust me, a well maintained 944 is probably more reliable than an SVT Contour.. I've been seriously been kicking around the idea of getting one for my daily driver/track car. I have a neighbor that has an 84 944 that he bought new back in 1984. It's always been his daily driver, and 18 years later, it's still running great. The specific issues with the cars are easy to find and pre-emptively fix (with aftermarket solutions). But it's not a car that's going to constantly break down on you.. (No, that was my old Alfa Romeo :>)
As for where to get started, try to find a 944 board.. Rennlist and the PCA websites are good resources as well.
People tend to believe that Porsches are unreliable, expensive to maintain, and all that jazz.. The truth is, people drive these cars harder than your everyday car, so sure, some parts will go prematurely. The 911s and 928s are expensive to repair, but the rest of them aren't so bad.. Sure, it's more than a Focus, but look at what you're driving. You have to pay to play.
If leasing is an option, I know there was a great promotion going on in NY a few months back, lease a Boxster for $399/mo, with like $3000-4000 down. The promo might be over, it was something they were doing to move convertibles in the winter months. Nothing beats a new car with a full warranty.
