The skidsteer is probably the most versatile machine to have, lot of things you can do with them.
4"-8" trees, sounds similar to what I have here, my preference would be for a heavier track type tractor, with side push arms, not a 6 way, for the clearing work, followed by using a root rake on the same tractor, to break up and clear the roots. Clearing in general can be nasty work, I like a bigger heavier tractor. If the trees pop out without too much trouble and you don't lose too much dirt with them, stable well drained soil conditions using a larger track type tractor is one productive way to do it. Some of the more modern methods where contractors use buncher/feller machines and tub grinders,or other tree harvesting machines are real quick, just that you have the stumps to deal with and most likely has to be hired out to someone with that kind of equipment.
The road work may best be handled with a dozer and 6 way blade for grading etc., although a skidsteer may also provide good performance, I still like the dozer with a 6 way blade.
Depending on what the most common use is of what you will be doing at the place, it should be the most influental as to what you may want to own. The skidsteer may be the most useful for the money in the long run, but it may not suffice for all the work you need to do now, possibly rent or buy decent used,(use care when buying a crawler, make sure you know what you are getting) and re-sell later, think about what's the best for the long term when you buy. I like to rent newer equipment for production and fuel economy, but own older afforable ones for all around use.
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