Pretty broad question. How big of a trailer, tools, pit ride, how often are you gonna be pulling a trailer? how far? All things to consider.
If your pulling a small, light open trailer and just a car, a 1/2 truck will work. If your pulling a larger trailer, with other things on it and more often 3/4 ton truck is going to benefit you. I personally am used to 3/4-1 ton vehicals so pulling a trailer with a 1/2 truck doesnt feel right even tho its rated for it.
Finding a clean 1/2 ton in that price range is going to be much easier then a 3/4 ton.