Ok I have been an Arborist for 11 years, worked for a company, did contract climbing, and now run my own company. Just imported a spider lift from Europe this year, got tired of climbing.
To run a service that actually makes money, you need around 3 years of climbing experience, and you need to be a decent climber.
You need a truck, with box, preferably dump, and a chipper. I have done the trailer route and it sucks. Also takes too long.
You need 1 climber minimum and 1 grounds men minimum, no solo work, that is just dumb. Solo workers are dumb, they get paid shit, people don't respect them as professionals, and its super dangerous.
2 million liability insurance should cost about $1200 per year to start.
You should be charging minimum $100 per hour. But its better to price by the day. You should be making at least $600 - $800 per day, starting out. That is a short day 6 hours or 8 hours normal day. You work your guys 10 to 15 hours, per day and they will quit. Then you have to train new guys, not fun.
Advertise, most tree companies suck at advertising, find cheap ways to advertise and do a lot of it. Yellow pages is a scam, kijji or craigs list shit customers. Paper advertising is good, billboards are good, small signs are good, word of mouth is good.
Rule of thumb when pricing, look at the job, first price that pops into your head, then add 20 percent to the number.
If its a job that takes a day, price for day and half. If it takes 2 days price for 3. If it takes 4 days, price for a week. That way if it rains or something breaks down your ok.
Price high, you don't need cheap customers, let the other companies deal with them. Don't undercut much, it devalues the business. Let other companies have the shit jobs, you don't need the hassle.
Avoid debt.