Welcome! C8s are great but definitely troublesome with their tranny issues ;)
As far as Supra goals - downpipe and tune. I would get this before an exhaust system imo. $200-300 downpipe, 400-500$ mhd/bm3/ecutek tune and you're easily set at 500 (to the crank) along with stickier tires is a...
Yeah, pass. Also those wings are tacky imho.
Unless it was the andro wing which looks nice. But aside from that... I'd just slap on a ducktail/bill one that's nice and subtle.
My thought process aswell. I don't think I'd be buying a dedicated sports car after the Supra for quite some time. Most likely a g80/82 M sedan or M suv.