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Although I don't own either car, I have driven both and have done a lot of research over the last several months comparing these two specific models because I am also debating which one to purchase.
One thing that I have found is that early 996's are really reasonably priced right now. And that is interesting because the '99-'00 996's are actually the more reliable because they have double-row IMS bearings (as someone already pointed out). So the rate of failure was much lower. But, since all the porsche enthusiasts out there HATE the 996 because it is the first water-cooled 911, the resale value has really tanked over the years.
Although that is bad for people who bought them new, it is great for us today. And in all the looking around I have done, I have seen a handful of '99 996's with <50k miles for asking prices between $22-28k. In my mind, that's a bargain.
I personally would rather buy a used BRZ, but the used market is very inflated because of the extraordinary demand for the twins. It's understandable, because they're great cars and are brand new models. However, you're not going to find any bargains out there. Maybe when the 2014 is released the used 2013's will start to come down in price.
So, for getting the best value, I'd go with a 996 with <30k miles and a history of being well maintained and driven weekly. They're out there. You will pay more in maintenance, especially compared to a new car, but the driving experience is tremendous (better than the twins, IMO). Also, since I'm seeing early 996s selling for the mid $20k pricerange regardless of mileage (examples with 100k miles selling for $22k, while examples with <30k miles selling for $26), it seems like they are nearing the bottom of their depreciation curve. So, let's say they never become a classic, and never appreciate in value. Well, you get an amazing driving experience and sell it in 5 years for a loss of $10-15k. You'd be looking at the same loss for buying a new BRZ/FR-S. In five years, they'll be down to 40% of their purchase price. In the end, then, it boils down to whether or not the enhanced driving experience in a 996 (again, my personal opinion) is worth the additional costs in maintenance and gas over the period of your ownership. If you do your research and find a stellar 996, I think those costs will be low and will make the driving experience well worth it.
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