Before the used car market went (temporarily) insane, I was looking at 996s. $35K could get you an absolutely pristine C2. At that price point, a high mileage TT was within reach. Something with 200K miles would've gone for maybe 10K (assuming no engine rebuild).
The IMS can be replaced with one that won't fail for $3K. A lot of cars already have that done. Also, the 99-01 cars have a different IMS design that supposedly is much more reliable. My understanding is it's really only the facelift cars that need it.