Advice on how to approach the job. Need to drop a tree

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Whenever I fell a tree with crazy limbs I try to cut them off with my gas powered pole saw and extension or my very long manual pole saw. Maybe even climb into the crotch to get more limbs than you can from the ground.
 
Lots of good advice, really hard to say how to cut that one without being there. Pics only do so much.
gotta watch if you take one at a time, weight can shift and others can let go the opposite direction.
Same for taking it all in one, some can let go before you’ve finished your cut.
 
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Having taken down a 5-trunked hedge tree, that part doesn't bother me... just cut each one as its own individual tree...but probably I'm just too dumb to know better. The big concern to me is all those dead branches way up in the air. A tiny bump or twist as you cut ...or even worse if any happen to be interlaced and one trunk moves while the other stays...could send a large chunk straight down. No way to outrun that!

From what I can see from the pics it doesn't look like a particularly difficult job. I'd just do a plunge cut as high as I could comfortably reach for each main section. HOWEVER, you point about "...a large chunk straight down. No way to outrun that!" is a critical factor and I couldn't agree more. Might not happen, but are you willing to bet your life on it?

I have a similar large, very dead Elm tree here that I'm going to take down later this week. I plan to tie a long bull rope on individual sections of the tree and hopefully pull down one section at a time with the tractor. But even there, not comfortable spending any time under the tree even to fasten the rope!
 
Yeah I would try pulling it down if you have equipment to do it. If not I would hire someone. Looks scary to me for sure
 
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Yeah I would try pulling it down if you have equipment to do it. If not I would hire someone. Looks scary to me for sure
Means a lot coming from bholler himself.
I don't have heavy equipment, just john deer 500 series tractor and come along with 100 rope that I've ordered. Had a tree guy coming today. He will do both trees, chip the small stuff, and leave the wood on a site for $1500.
 
I guess $1500 is Ok for two trees to be taken down , chip small stuff and leaving good wood .
 

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For that kind of money I would be doing it myself
But I won't say that because someone will jump all over me for saying it
 
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The ash tree, wouldn't be worrying about a barber chair so much just make sure you go at it with a saw with power and go through it quickly - use the lean on each portion it's three separate trees there's not going to be anything holding them together. What I would be worried about though is the limbs on the upper part of the tree falling straight down to the base of the tree (widowmakers) - possibly after impacting one another. Probably best to throw lines up in them, do small face cuts and pull it down with a truck. If you use a weighted throw bag and get it up in some of those upper portions you'll likely at least be able to pull down the upper parts of the tree, which are where the danger is if you're cutting at the stump. Then you can cut at stump afterwards