Starting a tree business
Hey jay, hats off to you for having the guts to start a business. I read through your list of estimated costs and I think you can start out for a whole lot less. For starters, buy yourself a good quality, mid-size chainsaw and a climbing harness/rope/carabiners. Go out in the woods around your town and cut up a few dead and fallen trees. Check with the forestry service or the cops to find out if you need a wood permit to do this. Get familiar with the chainsaw. Make sure you take someone with you in case you have an accident. Even better if the person you take with you has experience running a chainsaw and can show you a few techniques. READ THE OWNER'S MANUAL FOR YOUR SAW. It will tell you how to safely run it and care for it so it will last, and most importantly, it will tell you how to not cut off your leg.
Once you get pretty handy with the chainsaw, start messing around with your climbing gear. If you have a decent sized tree in your yard, practice using stuff like a throwline, friction saver, ascender, figure 8, prusik hitch and your harness to get a rope up in the tree and safely tie in. Practice belaying while on the ground. Step off the lowest rung on your ladder and belay your butt to the ground a few times, then move up to the second rung and do it some more till you figure it out. Now that you know how to run a chainsaw and you can climb, read up on how to prune a tree. Keep in mind you will prune fruit trees differently than shade trees. Now you are ready to go to work. Offer to trim your parent's trees or use your wood permit to go out and prune some forest trees. Put the branches in a trailer and dump them at the city green waste dump. At this point you're not ready to buy a 6,000 dollar chipper. Now you are ready to do this for money! Ask around the neighborhood to see if anyone needs their trees trimmed, or taken down. You might have a couple of friends who want to help, so show them what you know and let them do the easy stuff on the job (easy=cleanup and limbing). You'll want to take down some smaller trees, under 25', so you get the hang of dropping branches and trunk sections, because when you do larger trees, especially near homes or buildings, you have to be careful not to damage them. Put off doing big take downs until later when you get a little bigger and can afford business insurance. Again, read up on how to use rigging to get limbs and trunk sections down.
Okay, now that you've done a few jobs and made a little money, you might decide you want to do a full-fledged business with this. In that case, decide on a business name and register it with the city and state, get a tax I.D. number. Buy insurance for your business. Talk to a lot of people and let them know that you do trees. Keep in mind that if you're serious about your business, and you've taken the time to learn how to do it, it will show, and people will start referring you.
Work on your own for a while at first and get your work system down. It will start to occur to you how other people could do some of the work you're doing. Find some friends who want to earn a few extra bucks helping you and put them to work on a tryout basis. This will give you a good idea of how to have employees. If this works out pretty well, you can plan to hire some people. At this point, sign up for Employer's Insurance (workman's comp). You don't have to pay anything on it until you hire people, but it's good to have it lined up.
Now you can do the bigger takedowns and stump grinding, and money will start coming in. Keep learning how to improve your work. How you grow it from there depends on you, your work ethic and business mind. Down the road, you might be keeping enough guys busy that it's time to buy a bucket truck and a chipper for larger jobs you can reach from the street. A business grows like a plant-or a tree-not all at once, but little by little. Accept you will have some bad days, that you'll be stumped once in a while with certain aspects of your business, and that you'll figure out a way to make it work. Even if it all goes to Hell, you will learn from all your efforts, and you can apply those lessons to your next venture. The sky's the limit for the person who decides to create something. Good luck!