I love my '00 non S with Tip. I call the Boxster the new 914. Call it whatever you want, I don't care, but as a 914'er since '78 (a time when many 986 critics here were still requiring undergarment changes by a 3rd party
), I feel I may have a resonably qualified perspective. After all a 914 was my only car from '78 to '90.
The Boxster has great handling, great heat & air (including great defrosters in damp weather), not as much trunk space as a '14 but still better than a tail dragger, eats rear tires though (10-12k miles is all I can get). The more I live with the Boxster the more 914'ish it seems. Yes it may not hold value as well as an aircooled Porsche, but that's only if you plan to sell. Which by the way Britt you can have mine for $25k, with a tick over 30k miles, new rear tires, sport package, 17's, always garaged, and lots of other goodies. Yes, I know it's more than the going rate, but I really don't want to sell!
The answer to your question is that you can probably find a decent Boxster for a fair price right now. I wouldn't get anything less than a 2000 though, and of course get the newest, lowest mileage car you can afford. If I can ever make it to a Bluegrass event you are welcome to take mine for a drive.