I believe new is best.
I pull my trailer with an 05 Wrangler unlimited. Installed a windscreen behind the front seats. This created a pick up cab space with a pick up bed. Large enough bed for me to get buy 90% of the time.
Having a pick up would be better though I can not afford payments. Jeep has been trouble free so I have no desire to replace it with a used PU.
However my son works with a guy that is the original owner of a 94 F150 RWD 85,000 miles. Suppose to look like new and he told my son he was thinking of selling it for $1,500. Told my son to get it when the guy makes up his mind. Has 299 ci straight 6, 5 speed.