I'm actually about right where you are. I test drove a Vette and hated it. Very fast yeah (too fast really-- couldn't open it up without risk of going to jail)--I'm in the camp that says it's more fun to drive a slow car fast than a fast car slow. but the worst thing about it was the interior and overall build quality---it's SOOO cheap. Just looking at that disgusting cheap steering wheel every morning would have made me regret my decision. Was looking for something more refined, better build quality with handling as my number 1 priority. Also having good storage as my wife and I like taking weekend mountain getaways.
Fast forward 2 months and I test drove a MY09 Boxster w and w/o PDK. I fell in love with her instantly---then she showed me her $78k sticker price! We had to break up... So now I'm looking for late 986 (your 2001-2004 range) or early 987 (2005+). There are several threads here addressing this very question--search for them. I'm leaning towards 987 due to the improvements made that I like (especially the interior). But something I've learned from this great forum the past couple of months ---if you are "scraping the bottom of the barrel" to buy this car---then maybe it's not for you. parts are expensive and repair by a shop will be expensive and you need to plan for something bad to happen. Like Lordblood said, it's no Toyota. But obviously the potential for repairs is greatly offset by shear driving pleasure---as evidenced by the fact that they seem to hold their value pretty well. If these cars had serious reliability issues, I would love to be able to find my MY05 S for $10k
...but alas...they're still in the low-mid 30's for a model in good shape.
P.S. I'm really hoping for 987 with CPO warranty!! at least I get some piece of mind for the first few years of ownership..
My $0.02 as a future member of the club (hopefully)