1997 Boxster from private seller or 1999 Boxster from a dealership?
 

The 97 only has 43k miles on it and is selling for only 9,000 by a private seller. That seems a little off to me. The 99 has 61k miles on it and is selling for 10,000 by a dealership which seems like more of a safer buy. If I was to buy the 97, what should I look for as far as defects and failures go? Both sellers claim their cars are accident free with a clean carfax to prove it. What seems like the better deal if I was to buy one or the other?

I hate to say "it depends," but it truly does. Both present their own concerns. A carfax is always helpful, but never trust it 100% or use it as your single source for a buying decision. The safest bet for any purchase is a pre purchase inspection from a reputable shop or Porsche dealer. I assume both are cosmetically decent or you wouldn't be seriously considering them. Whatever issues may be present are likely not seen from the surface. A good test drive and PPI are the best moves.

I'm with Chris on this one. PPI is the only way to go really. I don't know the laws in your state, but here in Texas a dealer is required by law to tell you if a car has ever been in an accident. It's part of the paperwork during a purchase. That helps as far as purchasing from a dealer ( at least as far as hidden frame damage is concerned), but the inspection would still be the best overall, in either case.

*edit*

That private seller is right at blue book for a good condition 97 with 43,000 miles.

All of the above makes sense. PPI is a must to check for problems and accident/repair history. Ask to see receipts for work done - more likely available with a private seller. It is possible to get them from dealer(but they may come back with privacy issues-no harm in asking). If there are deficiencies on the PPI, use that as a way to bargain a better price. The $$$ you save you can put away for the future repair fund. Don't limit yourself to 2 cars. Take your time.
My 2001 Boxster base I bought a year ago had 34K miles on it. I budget $1-2k a year for maintenance. Good luck and enjoy.I prefer dealing with a private seller.

I truly dont always agree with a PPI, all the issues I have had with my car would not have been caught by a PPI (alarm, flywheel wear, IMS bearing going south) you can educate yourself enough to perform your own PPI for the normal problem areas.

A PPI probably would have caught these issues though that I overlooked-
missing air deflectors in front of the front tires and the broken fuel door actuator (but the PO did point that one out to me)

A lot depends on the knowledge of the buyer. In my
case I had little knowledge of the Boxster and the PPI caught leak in RMS and CV joint leak. So $200 spent on the PPI to catch at least $3000 of potential repairs was $$$ well spent to negotiate a better price. Each one to their own.

I own a 97. Buy a 98 or newer. The subframe on 97s is weak and the 99 has side airbags n the doors. They figured out a lot between 97 and 99.

I've had a few 97's over the years and liked them just because they didn't have the extra air bags. I had not heard or read about the sub-frame issues before.

I agree with with R/N; buy '98 or newer.

I wouldn't base much of anything on squeaky clean carfax reports...check the title and make sure it's not a salvage, and that'll at least tell you that the car is not likely to have ever seen any substantial damage.

My 97 had a few thousand miles less than the one you're looking at, and I think that price is pretty decent if the car is in good shape. You could probably get it for a bit less, especially if you find anything you'll have to immediately put money into (very likely for a 15 year old car). If the seller has a good track of maintenance records that will be a very good reassurance for its upkeep, unlike mine which literally sat in a lot for 5 years barely ever moving.

I'd hold the dealer to these same standards, but the advantage with the dealer is that you may be entitled to a few months of warranty after the purchase to fix any issues you find. In my state any vehicle purchased for over $3,000 gets 60 days of warranty by law, unless you choose to purchase the car "as is" and take your lumps. Find out what your rights are when it comes to a dealer purchase, and see what the dealer is willing to do as far as a warranty if it doesn't come with one.

Check the driver's door jamb for the placard with the build date on it. It's possible that the very late builds from model year 97 had the updates that came from 98 onward that fixed the frame issues that preclude the 97 from using 18 inch wheels. There's no good way of knowing, unfortunately, but it's at least a possibility.

The inspection is absolutely the most important thing to do. I didn't do this when I bought mine and although I was lucky, it could have been a horror story too.

Make sure that the person checking over the car knows Boxsters well. Like any car, they have their quirks and common problems, so an experienced person will always check "the usual suspects" that someone else may miss.

Best of luck and enjoy your purchase, whatever the decision may be.