a good diesel will probly be more than you will want to spend for a first truck. the mid 90's powerstrokes are pretty reasonable. a regular cab long bed probly wouldnt be too big for ya.
on a small budget, ive had great experiences with the 88-98 body style chevy pickups. decent power, pull good and handle a trailer good, and they take a lot of abuse. parts are really cheap for them too so theyre a reasonable older truck to own. ive had 4 of em. you can find those trucks with the 6.5 diesel for pretty cheap. they do pretty good, but i would only recommend those if you know someone that is mechanically inclined