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Yeah I suppose your location has a lot to do with getting rid of waste. I have a chipper and it's a beauty but around here if you can find a big enough spot to burn all you need is a match some beer and a few friends to watch the years work go up in smoke.
 
Assuming you have enough experience in both the tree world and the business end of things here is my 2 bits. Contrary to a few suggestions I personally would never buy used gear period. Always buy industry standard stuff ie. MS 200T not some cheapo saw. Don't invest to much to fast it will give you time to learn whats needed and whats not. The basic gear would be all the climbing junk like saddle etc. should set you back a G note. You will need 1 climbing rope, 1 bull rope and a utility rope 1/2" is fine. A spool of 1" tubular webbing and a wack of Biners sport,locking and non locking that will be another G note. You will require a 1 ton dump truck( get this BEFORE some moron tries to sell you his piece of **** bucket truck) as you need to remove branches etc. and believe me hand bombing on and off the truck is bullchit! Don't bother with a chipper in the beginning it's not needed. You will need to secure a dump site for all the trees you will be killing try leasing a spot from a farmer don't use logging roads it gives tree workers a black eye! Insurance is a must don't play if you can't pay you will be screwed if something goes bad. Extra stuff that pays LARGE dividends are things like BIG SHOT, Silky saw, blocks and slings. I would say a guy could start from nothing and be logging in say....10 G's. The only thing I would buy used would be the Chevy 1 ton dumpy!

Then it's time to bust some ass and make some squirrels freak out like back in Nam baby!!!

I guess it depends on where you live. Doing legit tree work around here would be nothing short of laughable without a chipper. And I'd have to turn down about 50 percent of my jobs if I didn't have a bucket truck. Situation certainly dictates. Also, I buy 99 percent of my equipment used, and I make out extremely well, if you have half a brain, it's easy to discern the good stuff from the beat. I wouldn't buy used ropes or climbing equipment though.
 
I payed $10 to get rid of a toyota bed full of trimmings from a jap maple the other day (couldn't fit a chip truck in the driveway, and road was crazy busy). I imagine that could get pretty expensive pretty quick doing takedowns! lol.
 
Guess I should rephrase a bit what I said earlier. When I said "don't buy anything new" I was referring to heavy machinery. Truck, chipper, stumper, crane, skid steer, lift etc. It's not a good idea to buy climbing or rigging gear used unless you can be very sure of how it has been treated. Chainsaws are a different story and I think that would depend on your skill level with small engine diagnosis and repair.
 
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