And how long before rebuilds? Not to mention comfort.

That’s...a tough one. I’m going to say SS. 

I own an SS and in person the SS looks very sporty, all it really needs is to be lowered, plus the sound will prove to anyone it is not to be messed with. I just saw my first two stingers in person and I have to say that it didn’t look very good, not anything close to what the pictures look like. Also the LS3 in the…

The only people who would get the Stinger GT over an SS are those overly worried about exterior styling.

100% no question the SS.  Hell, I wanted to buy one new, but I was in a cash crunch and by the time I sorted that out, the manual was gone.

V8, RWD, manual, anonymous “under the radar” styling - SS, no question

SS any day. The Automotive Gods have blessed it with that amazing V8.

I think you forgot a car that is actually comparable.

Stinger GT vs. off-lease Chevy SS?

CTS-V is a perfectly good answer. Even better, see if he can find a CTS-V wagon. I know it is rare as can be, but there isn’t a single sedan that hasn’t been improved by being a wagon. However, I’m not sure why he doesn’t just get a used SS with a manual. They can’t be that unobtainable.

CTS V is the correct answer.