I can only tell you what I've found with my Supe as I have no experience with the Skylines.
.
.
other than sitting in them at the dealer
(was looking at Impreza, older Evo's, R32, GT4 and the Supra TT) and not being impressed
- very much like the Impreza and Evo in that the interior is very much like a normal saloon car; although i expect some folks like the fact you can get 4 people in
- despite there being 4 seats in the Supe, you'll NEVER get anyone older than about 3 in there!
Anyway, the Supra is not really in the same category as the MR2 Turbo
(nimble B-road blaster) or Skyline
(nutter 4wd drag mobile); to my mind its more like a Japanese Aston Martin
- a big GT cruiser, with a silky smooth straight six.
I'd also reccomend you try both the auto box and 6 speed versions of the TT; I'm a dyed in the wool manual shifter
(take a look at my profile).
.
.
but the auto box of the Supra is one of the best
gearboxes I've ever used, never mind the best auto box.
Also, for me, driving in a lot of traffic and stop-start around Newcastle, its a dream.
.
and certainly no slower in real world terms
(~5.1 compared to
~4.8 to 60, big deal; who wants to burn clutches out at that rate every time?).
For me, IMO, the Supra is the classier car, the Skyline always looks like the turbo nutter mobile with its sharp angles, spoilers and wings.
Be warned though, running one is expensive.
I get, at best, 27-28mpg, when driving like Miss Daisy.
But the noise of that straight six when turbo no.2 comes online is fantastic!
seriously i think with all those options you'd be very happy 
