Hi Rich -
Hey, a couple of people messaged me and suggested I give you my $.02 worth on a machine to help you in your tree work. I sent you a message this morning with a little info and my phone numbers - I'd be happy to give you some help.
I'm really pleased with my setup - I included a link to this thread -
5030 "skidder" pics - the "tree-bota" in action - in my message. It shows my 5030, set up with a Bradco brush grapple on the front, and an Implemax 4836RW grapple/winch on the back. Check it out if you get a chance, and feel free to call me.
I'm pretty much thinking that a CUT is probably your best bet. Most of the tree guys around here use tractors; some use skidsteers (I don't recommend that route, tracks or no), and at least one guy uses an ASV, which does have its advantages (very light "footprint"). I still think a CUT might be your best bet, simply due to the fact that you can carry things in the front and back, and that really speeds things up. With nice wide turf tires, you'll do VERY little damage to all but the softest lawns, and they're very good in the snow (especially with chains), and not bad at all in soggy conditions, or even in the woods.
I would definitely, absolutely, positively get a hydro tranny, and the biggest tractor you can manage financially. You're going to need a lot of loader capacity, as well as 3PH lift. That lead me directly to the 5030. I just think Kubota hydros are impossible to beat, and I don't know of a loader stronger than the 853 that you can get on a hydro CUT. I do like the JD Twenty series, but I believe the 5030 has a little more lifting power front and rear than the 4720, and it's a very simple, rugged machine.
If you end up with a CUT, consider a Bradco brush grapple for the front, and maybe a Beaver Squeezer grapple for the rear. I think you're going to want to be able to pick logs right up off the ground for residential tree work, as opposed to dragging/skidding them. Some guys use forks on the front loader, but that never really made much sense to me; it's just really nice to be able to grab stuff with a grapple.
Good luck, and feel free to ask me any questions you might have,
John