I have wondered what's better, tires or tracks and I guess you definitely cleared that up. For the record, I'm certainly leaning towards just hiring someone to do the grading. I've asked a couple friends of friends that know how to operate a skid loader well, and they've all told me I could do it (might take an hr to get comfortable), but I'd definitely prefer to just pay someone 800-$1k if it can be done in a few hrs. We'll see, at this point I might just push off the project a year or two so I can dedicate an entire weekend to the project.
Renting the sod cutter and removing the sod I'd imagine will take me the better part of a day. Then the grading, then relaying out all the sod with some top soil. While it does sound like fun to rent the bobcat, I'm also realistic. We'll see what happens. I do feel a little better though hearing from a few people that it isn't that bad.