What works for me, as a contract climber who does not own any big equipment, is I partner up with local guys when I travel. I get guys lined up everywhere I go to sub the hauling and do the cleanup, when I am selling my own jobs. (big newspaper ad right now). I figure about half of every takedown bid for cleanup, and this pays ALL the labor. I make good money, and they make good money. on pruning jobs, I leave it curbside, and send the crew around to clean it all at once after I have a couple done.
plus, 10-99's shed us of tax obligations.
Find you a landscaper guy with a skidsteer, and sub it til you are ready to buy, not another tree guy, he will be too tempted to take the walk up jobs.
This works everywhere.
I work with this guy 2-3 days a week, he has 3 different machine available, and he just built a grapple, and is buying a chipper next. he smells the $$.