You should be able to get a 2500/F250 1990-2000 Dodge, Ford or Chevy in that price range, give or take $5000. I would also consider a diesel for the gas mileage. However, with a diesel, maintenance costs will be higher. But, usually the diesel will out last a gas engine. Diesels will also have better pulling power. Brand is personal preference. I have heard good things about the Chevy DuraMax and the Dodge Cummins.
Here at Fedex, all of our diesels are the same engine as the Dodge trucks. The newer ones are very quiet but that is the 2004 models.
We have had very few problems with regular maintenance.
The Ford Power stroke in the years that you are looking will be the first years out. So expect some issues. Also, I think the DuraMax came out around then also.
As for Ford trucks they have no turning radius especially on the club cab with the 8ft bed,
Chevy’s are better but personally don't like the styling. The newer trucks do look better and are better laid out in the cab. But still not a big fan.
Dodge is obviously the truck of choice for me, even with the 5.8L gas engine I have not had any problem towing.
In addition, it has a far better turning radius than Ford. Also, consider 4x4, you don't need it all the time but it is sure handy in a pinch. I have never had any problem launching my boat at any launch. The 5.8L gas motor sucks the gas, but it sure is a workhorse.
Just my two cents
Oh and another thing check the value of any truck before you go talk to anyone at
www.kbb.com that's the Kelly Blue book site you can get values on trade-ins, retail, and personal sale.
Good luck shopping