FYI, a 997 GT3 is terrible for around town driving.
Owning both, I can tell you with absolute certainty that an '88 Carrera is easier to drive around town. Maybe not as "comfortable" given the lack of creature comforts compared to a 997, but an easier drive. The clutch and steering on the GT3 is not suited for a daily.
As for car rec's, realistically all manners of Porsche are probably going to see relatively strong pull back given the recent run ups, with the sole exception of:
- super collectibles (not relevant)
- 1999 C2 Convertible triptronic (can't go any lower)
The 997 Gt3's saw a huge run given the initial form of the 991.1 GT3's and are going to get hurt moving forward as both see negative pressure on pricing. I'd guess the 991.1 will move about $40k over the next 5 years, followed by 997.1 GT3 around $25k and 997.2 with the best staying power around $15k (landing them around $85k, $75k and $90k respectively).
If you want the best value today, find a tracked 996 GT3 for around $60k; that should hold value best (but wins the award for worst interior by a long shot, so may be a no-go for the wifey).