Hi Will,
I recently bought a NA Aerotop so understand where you're coming from. I previously had a hardtop NA MR2 which I had for about 3 years. All the time I owned it, I regretted not getting the T-Bar or the Turbo version. So when looking to get a Supra I was admant i'd get a TT Aerotop, then saw the prices they were fetching . So it was down to a choice of what would I rather have, a (kind of) convertible or a hardtop that looks exactly the same, but goes faster.
When I first got the car I was impressed with the performance, but have got used to it far too quickly. On a couple of occassions I've had people sat up my a**e and thought "I'll show you matey" and booted it only for them to keep up with me (e.g. rep in a 328i BMW. oh the shame!!!)
I think it all depends on what you personally want from a car, if you want good looks, reasonable performance and a summer cruiser then the NA Aero is perfect. If you lean more to the performance side then the TT is the one to have. Or if you want both and you're a rich jammy git then get an Aerotop TT.
I think it would be worth test driving a few of both the NA and TT so you can be sure you're making the right decision.
Oh and BTW insurance is way cheaper on the UK TT than the NA for me too!
Matt