Someone named Joe Brown at Wired complained in a print magazine article (it appears to be a blog printed on some sort of dead tree material that you can get in exchange for some other green dead trees...it is all very arcane, but I'm sure there is an old person you can ask about it down at the nearest senior center, but you can find it online here) that there are no good small pickups for his hauling needs. Prove him wrong. Find a cheap small truck that Joe can drive everyday. Budget ~$5000.
This is just the first page of the article, I'd share a link, but the entire thing is still in print version Wired magazine, perhaps it will eventually be added to the digital archives. You should go buy your own copy, but in summary Joe says quite succinctly "I'm not a ranch hand, I'm a yuppie carting my hobbies around." Every pickup from major manufacturers has gotten big and most are overkill for the yuppie city dweller who just needs something for a trip to Home Depot to buy some wallpaper, maybe get some flooring, stuff like that. Maybe Bed, Bath, & Beyond, who knows, if you'll have enough time.
For my money I'd pickup an 80s Hilux like this 4th generation 1988 Toyota SR5 4X4 pickup here on eBay bidding for $6,087 with 1 day to go, located in Snohomish, WA. It has 120k miles on the odometer and should be good to go for another few hundred thousand with basic maintenance. What can you find? Put them in the comments below.
Update: Joe replied to an email and says he is looking for something in the $5k range and he is in the SF Bay Area, but would fly anywhere for the right truck and drive it home...but so far he has traveled a thousand miles, looked at 20 trucks and hasn't found the right one yet.