Nothing seems like hard or large work. Personally i would buy a nicer track skid steer, cat 299D or JD 333G. They have so many attachments you can do 90% of the work with them. Rent a forestry head for taking down the trees or a brush hog for other clearing. Post hole auger isnt an issue, grapple bucket for moving trees, can even get a dozer blade for grading. Also super useful around the farm for moving large hay bales etc. Then rent a excavator for a weekend to do your culverts or other deep digging needed. Can even get GPS setup in the newer skid steers to help with grading if your looking to get something really flat.
00 XJ D60, S10.5 built as cheap as possible
14 F350 dually