Whatever you decide, I hope you do go the 'trailer queen' route. Decide what you want, buy it or build it - whatever suits your fancy. But, by all means, drive it everywhere you go - rain or shine!
Like you, I always wanted an older model vehicle for nostalgic reasons. But, I always leaned toward older trucks. I spent years on the internet searching for my 'perfect' vehicle. Even though I am fairly skilled when it comes to working on older vehicles, I decided to get one already finished and then simply add my personal finishing touches.
I purchased a 1957 International S-100, half ton pickup about 18 months ago from a older gentleman in MN who had taken an old Iowa farm truck and rebuilt it from the ground up. I wanted something 'different' that wasn't your run of the mill everyday Ford or Chevy. Has a matte black finish, 305 Chevy V8, 700R4 automatic transmission with OD, dual exhaust w/ glass packed mufflers, power steering, tilt wheel, Pioneer AM/FM radio and CD player, bucket seats with center console, and most importantly AC for those hot Columbia summers. Can't go anywhere without people wanting to look at it, take pictures of it, and talk about it.
Just do it!