Seems LD1 and I are saying pretty much the same things about your project list.
That Ford is a good example of going with a full-sized machine, although it's not a low-hour machine any more and may or may not be wanting some major maintenance. You'd get your excavating and dirt moving work done faster with it than with a smaller TLB setup, but that option means you'll put more of the burden on your TO30 to handle the grading and leveling work with 3 point implements. If the old gal isn't up to that work, you might be shopping for another tractor anyways. Of course having two machines for a big project isn't necessarily a bad thing, if your budget has room for it.
Without having seen your property and the work to be done, I think it might get down to what kind of equipment you actually find available.
That Ford is a good example of going with a full-sized machine, although it's not a low-hour machine any more and may or may not be wanting some major maintenance. You'd get your excavating and dirt moving work done faster with it than with a smaller TLB setup, but that option means you'll put more of the burden on your TO30 to handle the grading and leveling work with 3 point implements. If the old gal isn't up to that work, you might be shopping for another tractor anyways. Of course having two machines for a big project isn't necessarily a bad thing, if your budget has room for it.
Without having seen your property and the work to be done, I think it might get down to what kind of equipment you actually find available.