For CUCVs I sometimes plan on driving back but usually use a friend's goose neck trailer to save on drama and so I don't have to coordinate for a helper.
For deuces etc, I plan on driving them back and am prepared to use a tow bar for short trips (ex.; Fort Drum=115 miles).
For longer trips, I have an agreement with a local heavy equipment hauler bring back anything that can't be driven. The price would be pretty stiff if they have to makea round trip and a lot easier to take if they can pick up on a return trip with an empty trailer.
To date, I've been fortunate. The only truck I "had" to trailer was an M1008 without third gear and reverse that was 320 miles from home. I didn't want to nurse it home on back roads at 20 MPH so since I was picking up a couple of trucks on that trip, I left it and went back a few days later with the goose neck trailer and dragged it home.
Ya' know....if you just go ahead and buy one, you'll figure out how to get it home!
Lance