Haha I may give it a shot this winter when there is down time. Trying to take on a few small jobs with what I got sounds like a good place to start. I do fine where I'm at farming but this is a dream I've had for a long time. Running saws, cutting and shaping trees are a passion of mine and if there's a way to do it as a profession, well that'd be great.
It has been over a year, did you ever get your tree business started?
> Get your CDL
This is one of the best pieces of advice given !
Your limit for a trailer will be 10k without it, which leaves you with a 7500# load, and if you get caught over the limit with a non-CDL trailer, you are in for an expensive lesson.
Buy a dump trailer !
Buy a bucket truck (likely a CDL) with a bucket where the boom doubles as a ladder, I think it is ALTEC?
ALWAYS wear a harness and safety strap inside the bucket. If you do not buy one where the boom is a ladder, you better know how to get down from your 40+ feet using a rope, your harness, and a figure 8 at a minimum. That includes getting down after you fall from the bucket. People fall out all the time from user error, getting struck with tree branches, get dragged out with tree branches, and they certainly break down enough!
Wait until the day you cut a branch or large limb and it bounces back off the ground and takes out the lift ! One of the hazards of people trying to win the Darwin Award while using ladders while cutting trees is the cut piece swings around (no undercut) and takes out the ladder on which they are standing.
This is Georgia so there is always tree work! I would say start by clearing tree lots for farms where you can just drop them, then buy a sawmill and remove the wood as lumber. This will pay for more equipment.
If you buy a dump trailer it will save a lot of time and you can make a decent income from firewood. You can even rent yourself out to Mexican roofing and tree "companies" where they can not have dump trailers in their apartment building parking lots or mobile home lots.
I started out by doing a neighbor a favor so her house would not get crushed by a group of pine trees that had already started to fall during a storm, one had already grazed her house, and we had less then 24 hours to remove them before the rest of the storm came through.
I told her there was no way I was cutting all that with an electric chainsaw and axe. So, I had her pay for a Poulan Wildthing 18" for $160, I spent my own money buying some 1/4" cable for anchors and winching, and I took down the remaining (3) 20"+ pines by dropping and pulling them into the cul-de-sac next to where she lived. Then had my kids come over and stack all the branches and rounds on the curb for the county pick up which was $75 if I correctly remember . So, I was in the business and I had (got in GA!) my start just because I wanted to help my neighbor so her house would not be crushed.
The insurance adjuster could not believe I did the whole job for $160, when it would have been thousands of dollars to have it done WITHOUT emergency pricing. So, because some of the front windows had to be replaced by the first tree that "brushed" her house and broke the front windows, he said he would replace ALL the windows in the house so they would "match" :-D
I started with an 18" Poulan Wildthing (commonly known as the purple pull-on-alot) on which I put on well over 100 hours doing firewood before blowing it up, and about $50 worth of 1/4 cable and clamps, and a 4x4 pickup truck that I used as a winch and anchor.
So, you certainly do not need to spend big bucks to get started, but, being willing to learn and knowing how to work safely without killing yourself or someone else certainly helps.
Wear a real chainsaw helmet with face screen.
Steel toe boots with a puncture proof sole.
--> CHAINSAW CHAPS <---
Good anti-vibration gloves