Thanks my first tractor purchase and I don't want to buy something I regret. I have lurked the boards here for a while and have found a common theme of don't buy something thats not powerful enough. My worry is buying too big, a bull in a china shop, the Massey being too big and heavy to go into the woods
I use my LS (which is quite a bit larger than either of the two you're considering) in the woods a lot....pulled many cords of firewood out this past winter (tons of dead Ash here). I haven't had a problem getting around, and between trees etc. There will always some situations where it gets tight, but you can usually work around those. Really, the only thing I've done was build a very compact counterweight, because I was using a box blade that would sometimes be too big when backing up, or working closely around a tree.
On the flip side, there a quite a few situations where power is at a premium, and you can rarely work around those....either you can lift it, or you can't. Unless you have a fixed requirement, like a barn door, or horse stall, that you have to be able to fit through, I don't think you gain a whole lot by going with a smaller tractor.
If budget issues factor in, I'd point out that you can buy a lot more capability for about that same amount of money, by looking at other brands. My LS was only $21,500, and a similar Kioti was only $1K more (obviously no MMM on either). You could probably do something like a larger tractor (something like a CK35), and a quality zero turn mower, and wind up with the best of both worlds for around the same price....a great mower, and tons of tractor power.....just a thought.