When I was between jobs, I ran into a guy who was a regular at my old job. He ran his own tree trimming business and asked if I wanted to do some work with him (I assume 90% of the reason was that I had a truck, and he didn't even have a car). He was definitely kind of a sketchy dude, and the other guys he had working for him were twice as sketchy. But at the end of the day, he was super knowledgeable about what he was doing, enough to be able to competently run a crew that was usually made up of different random desperate people every few weeks. He was amazing at talking to people he'd never met and most of the work we got while I was with him was by talking to surrounding neighbors on the jobs we were doing. The most I ever saw him charge someone was $500, but that included hauling the lumber off the property. Most of the jobs he did only ran about $200-$300 for a day or two of work. We always left properties looking how they did when we got there and never half-assed a job. If I ever owned a property with trees that needed trimming, I know exactly who I'm gonna call. Sometimes the door to door guys are just as good as the professionals. Suffice to say, if you're gonna get a service like that done, always get quotes from competitors in the area, and never pay for it all up front.