Welcome. With 2 celica's you should be able to nip to a dealers and try out a Supra or two and get to know them a little better or get yourself along to some of the Supra meets. Best of luck with your search.
Fwiw, I used to love my Celica's had several St162-ST182/ST185 models (the ones and last of the ones with the pop up lights). Loved the drive, reliable speedy engines, decent ergonomics and equipment and practicality.
With the Supra, its a step up in performance (with turbo models), the cars are still as easy as the Celica to drive, on OE 17" wheels I found the ride to be much better than the Celica's, a little bit more equipment and technically more advanced as a performance car. Only downside is, if you use the Supra as a daily driver, it won't be as practical (in terms of boot space even with the seats down) as the Celica but the fuel consumption, IMO, is excellent when driving normally.