Josh,
How much cleaning and digging is required, and when it is done, what will you use the tractor for. A lot of us buy a compact tractor that will do 85% of what we require, and farm out the heavy stuff. With only 5 acres, you really need to decide if you have several thousand dollars worth of backhoe work to do, or if you can contract it out for a lot less time and money. Also, I'm not sure what clean up work means. My guess is you mean loader work. I think most of us will want more detail on you property and your goals before we can guess at what will work for you there too.
Re. your land: Flat or hilly, wet or dry, fields or trees, sand or clay, big rock to carry?, stumps to pull?, digging a drainage ditch or a pond?, lawn to mow, gardens to till, snow to remove, yadda yadda.
You get the picture. I'll wait for your response before I offer my 2cents.
Todd