Phil - I own 5 986 Boxsters and a 996, and I don't lose a minute of sleep over them. I do have a slight concern with the IMS bearing ONLY as a maintenance item. Being a mechanic, you know - a bearing will eventually wear and need replaced. (Eventually, so will everything else, so treat it as a maintenance item and don't worry.)
I have the IMS bearing replaced when the clutch is replaced. Then, I don't worry about it until the next clutch replacement, which for me, will be a long time. The only other things I keep an eye out for is the water pump and the rear main seal. Replace the RMS with the clutch and that problem is solved, and somewhere along the line replace the water pump. I think those 3 maintenance items cure 90% of the problems.
Otherwise, the only thing I tell people is to remember that these little beasts were $60k cars when they were new 15 years ago. Today that $60k is prolly about $80k. While they are only a $10k car to buy, they are a $80k car to repair. Being as you are good with a wrench, I wouldn't worry too much.
I'll let everyone else bore you with stories of getting a PPI, buying the newest car you can afford, base vs S, blah, blah, blah. Find one you like, check it out and have fun. Drive it until it wears out, then go find another. Any year, any size engine, any transmission, they are a tremendous fun car.
Rick