Hi Jen,
Welcome to the forum.
I am relatively new to the forum as well. However, I have had a similar dilemma last year about the same time shopping for my first Boxster. I was looking for a well maintained used Boxster 2003-2004, preferably an S.
You have several advantages that I did not have.... you have already found this forum before your purchase and I do believe the current state of our economy is in your favor. I would take dcporsche99's advice and read the various links to MikeFocke and RandallNeighbor. They are a wealth of information.
I searched for about 4 months before I found my 2004 SE (Silver Anniversary Edition). The Dealership that I bought the car from did not know much about Porsches. It had 28,000 miles with all the maintenance records from a local Porsche dealership. In addition to the standard package of an SE (6 more HP, 05 S sized ventilated brakes, lowered suspension, wider stance with wheel spacers, short shifter, Litronic headlights with cleaner, Heated seats, PSM, GT silver metallic color with cocoa brown leather) it had as options... cruise control and Bose sound package.
I was not really looking for a 2004 SE in particular but this car was well maintained and the dealership knew very little about Porsches. They were asking 37,900 for it. I paid for a PPI and the car was sound. I haggled for about 2 days and knocked off 4K from the asking price and paid 33,500 for it. According to the internet this was very close to trade in price. I think I got a good deal but I still wonder if I should have pushed a little more.
For my haggling.... I maintained that this SE was essentially the same as a standard 2004 S and that this limited edition was not so limited (1,953 copies made in total). I also argued that this car would not hold its value any better than a standard 2004 S. They tried to pressure me and alluded to "other interested buyers". I did not have my heart set on this particular car and let them know I could buy another car by leaving the first day of negotiations.
So.... take your time. Get a PPI and search this forum. Very informative. My car has been trouble free except a broken seat heating element... replaced for free under warranty.