I have a 2003 Haulmark 24' trailer. I wouldn't consider anything smaller than 24' for hauling a B body.
You're gonna want to put some stuff in the trailer w/ the car and have some room for hooking straps up.

I also wouldn't want to pull one with a 1/2 ton truck either. The weight isn't as big of a deal as the wind resistance...as far as power goes. If you don't go very far or use it much, the 1/2 ton truck may be ok.
BIG difference in towing an enclosed versus an open trailer when it comes to power and MPG.


CHIP
'70 hemicuda, 575" Hemi, 727, Dana 60
'69 road runner, 440-6, 18 spline 4 speed, Dana 60
'71 Demon, 340, low gear 904, 8.75
'73 Chrysler New Yorker, 440, 727, 8.75
'90 Chevy 454SS Silverado, 476" BBC, TH400, 14 bolt
'06 GMC 2500HD LBZ Duramax