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, I've 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. I've 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