There are brand new (unsold) 2019 Boxster GTS's out there for $25-$30K off sticker with really great options. Could be interesting.

 

He wants a manual so forget the .1 T or TS. And why would a Ferrari be hard to resell?! There are many different models you know.

 

Another vote for a 981 spyder. If you don't need backseats, the driving experience cannot be beat. Manual, RWD, that glorious sound and drop dead gorgeous looks! Right in that sweet spot for price and not difficult to get out of (if you're like me and look for new toys every 6-12 months).

 

997TT. Just got one and already have a 991.1 C2S so I feel like I'm covering both sides of the Pcar equation. With a 6MT the TT is just addictive to drive and be in and I like the interior, to me it feels more like a mechanical experience, it's almost like driving a piece of machinery compared to how refined today's cars have become.

 

If I was selling my 991.1 to “upgrade” without going over $95k, I would be looking at 991.2T or better, R8 V10, or F430