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I absolutely agree with all of what Flavor 987S has to say with one exception. Financing isn't all bad, provided that you find a car below market value that you can sell for what you owe throughout the loan, and that you plan to keep the car long after the loan is paid.
As to the "S" question, I've never heard an "S" owner wishing he/she had a base, but there are plenty of folks with the base who wish they had thrown out a bit more for the "S".
As to year, Porsche certainly made each successive year a bit improved over the previous, but in the 986 series, the differences from 2000 - 20004 are not staggering.
One of the best suggestions out there is to find a car with at least 60,000 miles and good documentation of the service. Oil changes should be every 5000 miles!!
The most important question is probably how you are going to use the car. If it's just for top down, pleasure driving, PCA tours, fun rides with the spouse/SO, a well optioned base Boxster would be fine, and probably a bit cheaper primarily because of the tire sizing.
...but, if you have track, DE, autocross, spirited-driving-beyond-the-legal-limits aspirations, or the modification bug, you'll end up with "base-buyer's remorse"
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