I guess with the frost heading in the stump pulling season is about over. I have about 4 trees leaning toward the shop that need to go, so I'm thinking about how to rig it up for that. Maybe use a straight trunk and multi-ropes as a lever to keep the tractor and cylinder out of the crash zone.
Now think that through carefully!!!!!!!!!! felling trees is a whole different can o worms!
Personally, I don't think your rig has the "throw" to use it for that purpose as, if you find you have to pull the tree a few more inches when you have maxed out the throw of the cylinder, you up a creek with not much paddle!
I have a BIG logging winch and I admit I have pulled the stunt you are speaking of.......
The differences are 1)I can rig the winch far enough away from the tree (and at a 90 degree angle from the pull, by chaining a slider to an anchor tree) so no matter what happens, the tree CANNOT fall on the tractor.
2) also, the "throw" is more than sufficient to pull the tree completely over once I start pulling on it. IE; all the cable can be winched in, say several 10's of yards of it, such that once I start pulling, the tree IS coming down, or at least I can lock the winch such that I don't worry about it going the other way.......
I had a "leaner" threatening the house....... It was a big s.o.b. and it had to come down, (but it was NOT leaning more than a few degrees) I wrapped a choker around the tree as high up as I could reach standing on a step ladder (for max leverage). I pulled the winch cable tight and locked the winch. At that point the tree was already wanting to go the direction of the pull.
I snuck up to it and cut a pretty good wedge.... then put more tension on the winch cable. I snuck up to it again and started cutting its back..... left a good hinge on it after watching the back side cut begin to pull apart. Nipped at it a bit more and then gave it all the winch had....... down like several ton of bricks.......
I don't recommend this level of stupidity at all, but I had limited choice and I got away with it. I doubt I would try it with your rig.
There is a thread here about a guy dropping a tree on his Kubota........ it wern't pretty!