I painted my 66 15 years ago and I spent over $2K just for materials. That was with DuPont Centari and all DuPont prep under it. Base/clear would have cost more. Sanding discs, tape and masking paper, all brand name stuff too. Not cheap.
If the paint is as solid on the car as it looks in the pics but just dull, I'd try and buff it out.
IIRC to get the emblems off the vinyl on the C-pillars, the sail panels have to come off the inside to get at the nuts. That's 3/4 of the battle to change the vinyl and there isn't much vinyl to change compared to a roof.
If the paint buffs out and you change the vinyl, that car will look like a million bucks for just a few hundred.
Kevin