1) Rennlist was an excellent resource for me when I needed to find a mechanic at school (250 miles from my normal mechanic). Ask other Porsche owners, especially other owners with about the same budget. They should be able to point you towards good shops. Don't be drawn in to a shop that is Porsche specific. While that's not a bad thing, there are plenty of generic "import" shops with excellent mechanics. My 914 and 924S go to a guy who works mainly on Japanese cars but who has been a German car nut all his life. He has always done excellent work. Be wary of any shop that won't take at least a little time to talk comfortably with you.
2) If you buy a car that is in good shape (I recommend a pre-purchase inspection), then yes. Granted those $600+ belt changes come up relatively fast at 30,000 miles and the clutch is $1,500 when it goes, but those are really the only terrible things and they don't come up often. On a per-month and averaged-out basis, the 924S/944 isn't much worse than a Honda of comparable age.
3) My 924S is a daily-driver. It handles surprisingly well in the winter, the heater is excellent and if there's no accident damage or paint chipping, then the cars just don't rust. As long as you are wary with the car in the winter, there is no reason that a 924S/944 cannot be every bit as reliable as a Honda of comparabl age.
4) Not on a track you mean.
5) Get a Craftsman "mechanic's" set. No sense not having the basics. A pair of Vise-Grips is also good to have. You don't "need" the tools, but it's always nice to be able to take care of the small stuff.
6) Not that I know of, but separation is _not_ inevitable. Just be sure to _never_ slam the hatch down and never lower/raise it by just one corner. Lift at both corners and lower the same way, gently pushing down above the latch-pins to secure it.
7) Buy the best that you can afford. You'll end up about the same money-wise, but buying a nice car will be a lot less hassle.
What would I have done differently? I would have not bought the one I did. All the good signs were there, but I had a bad vibe and I ignored it. The PO was a divorced woman who had only bought the car because she wanted to rub it in her ex-husband's face that his alimony bougt the red Porsche he had always wanted. My $3,000 924S is currently a $6,000 car and it's sitting while the clutch gets replaced. In contrast, I bought the 914 for $3,600 and so far I have only put about $500 into it with the $350 for my new Fuel Injection system being the majority of that.
Aaron