You asked huge questions... First of all, the trim on the hatch (the rubber trim on the exterior) doesnt really seal much, nice to have but not a necessity. Very hard to find used.. new is too expensive. I live with mine being chipped in a couple places.
Second.. overhauled turbo usually means rebuilt and that can vary depending on who did it. No way to tell with the info you provided, but turbos aren't an extreme expense.. I would just be happy with what you have.. for now.
6 PSI and flooring it all the time? Wouldn't worry too much about the turbo.. worry more about the car. It's what we loosely refer to as driving the bag off it...
Straight pipes dont hurt turbo'd engines.. I think you are thinking about naturally aspirated (NA or.. non-turbo) engines (specifically the 7MGE). It needs slight backpressure to clear the cylinders on the exhaust side. 3" to 2.5" just means back pressure.. wont hurt anything really.. it just doesnt breathe like a full 3" exhaust will. Cant get the air/fuel in.. if you cant get it out.
Paint? Depends.. I am spending 6500.00 on body/paint on mine.. but mine is an extreme condition. Not everyone will have all the trim removed, paint the door jams, add a body kit, etc...
Simple paint job (with no body work) is about 1500.00 for a good one. However.. its a MKIII.. so you probably have rust issues (unless your lucky).
You can prep/paint the trim yourself around the windows. It isn't hard, but I dont have the "blow-by-blow" steps to do it or a recommendation for paint. Somebody here will have done it. (or.. you can search the forums)
Honestly.. just by your questions.. I would say.. dont do anything but maintenance on your Supra for a year.. read a lot of the forums (there's so much info here it will choke you), do a compression test and leakdown test to verify your engine state and retorque the headbolts if it hasnt been done lately.
The Supra is an excellent car, but its a steep learning curve to maintain/build it properly and can be very expensive. I waited 2 years before pouring money into mine. At that point I was sure the car wasn't a peice of poop and I had mapped the path out to get it done.
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