What size is your chipper ?
Chipper? I don't use a chipper when I'm climbing.
Joking aside, I just haul in a dump trailer because I'm not a full timer yet.
As for my market, it's a mixed bag of everything. Rural, small towns, cities of 30-100,000, hilly tight back yards are not uncommon here, and nor is a flat front yard. Bucket truck companies do fine around here, as do climber/crane.
I think I will go with a full size Cat 247/257 MTL. They are much nicer on lawns and backyard hardscapes then full size wheeled machine and even CTLs. And as long as you know how to turn, they can be just as nice on turf as an art loader - we're talking 4.5 psi on the tracks.
Between that, and an estimate that 20% of my work would be easy front yard access, 50% would be backyards with enough room for a full size, and 30% would be fenced back yards, I'd gladly drag 30% to the fence and have the reach of the full size to pick over the fence, or just remove a fence panel if possible.