Had Alfas and a 914 before I was married. 2 Boxsters after all the bills were paid and retirement secure. Love em.
Loved both...a '99 and an '01S. Only had two because I totaled the first...and jumped right back into the same car. Mine were very very reliable over 5-6 year time span and cheaper to maintain than a Honda and Acura I had of the same approximate vintage and miles over the same period.
Both I was 3rd owner.
Yes, I suggest getting to know a well recommended Porsche specialist for the Pre-Purchase Inspection. You want someone who knows the quirks of the car to let you know what it needs so you can make a fair offer.
The car is fairly easy to wrench on and there are lots of folks who help you with write-ups, diagnosis and on-line suggestions. Parts are no problem even going back to the '97.
You'll find about a dozen articles on buying a Boxster here
http://sites.google.com/site/mikefocke2/mikesporscheboxsterwebpages
Would I do it again...in a heartbeat.