Part of the reason I sold my high mileage Tacoma was the whole re-gear dilemma. The truck was awesome, but I didn't want to put $1000-$1500 (plus wheels/tires/suspension) into it with 210k on the little 2.7L. It might spin 33's a bit better, but then I'd be winding it out on the highway at 75mph.
If your building plans are such that they will snowball into lots of expensive mods, it might not be worth doing much more.
I bought a salvage titled Tundra with 169,000 on it. It was cheap, so I deemed it worthy. It can turn as much tire as I'd want to run (which is 255/8017).
That being said, I'm not going out on building it. I won't regear, I'm doing Bilstein 5100s, maybe some custom low-offset skinny wheels, and perhaps putting a camper on it. If in the event it gets wrecked or something I'll strip parts off it and they'll go on another. I didn't want to mess with a build that would make such a swap a pain (and add nothing to the value).