If I may…I would a recommend a Ranger in that price range…mine has been very reliable, gets good enough mileage, has a decent ride, and they can be had very reasonably…
I am worried about the Ranger/S10 not being able to haul what I need with ease. I also am looking for something that may have a decent tow capability in case I need to borrow my brother in laws trailer for an afternoon.
Im assuming you don’t want to drive to the Albany area for a truck but if you don’t mind pm love4boost on here. He usually has a cheap truck or two for sale at his dealership.
We used to have a long bed v8 98 f150 for our lawn care business and it did the job well. Probably a f150 from that generation or chevy 1500 would be your best bet (2wd)
4wd will probably be way more right now due to plow season. Or buy after winter and use 4wd as a selling point in Fall