Where are you in VT? I can show you my DK40se with Fransguard winch, and let you run it in the woods to give you an idea what you're getting into. Mine isn't for sale, but it might give you some perspective. If I had to do it all over again I'd go with a DK55, but I'd keep the r-4 tires (buy some ice pick chains). You should also budget in a grapple. You're going to have lots of slash to deal with and piling it up is good for wildlife, or burning, depending on your preference.
I like th hst, because it lets you concentrate on pulling logs, and operating the winch, and loader, etc. shifting is just something I wouldn't want to add to an already busy experience. On the downside, the HST doesn't have as much nut as a gear shift when pulling big hitches.
Another factor that you haven't mentioned but will need to be addressed is the need for enough tractor to clear a log landing, an old tricyle front or anythingless than a 40hp and yo'll be clearing a landing for about 20 years before you even get into the woods.
If you want to see a really nice set-up as far as armor etc go to Rick Wallace's website, he setup some DK's for utility company use, if I had had the money I would have had him armor plate mine!
No matter what only buy a tractor with a good dealer nearby!!!!