I am not sure what your budget is, and I didn't see you say how many acres you have (I'd assume a good bit considering a 300ft driveway), but you may also want to consider buying 2 machines.
A MMM is like a $3000 option on most of these tractors. And that would go a long way toward buying a Zero-turn mower. And they are MUCH quicker at mowing than any of these tractors will be. And you wont have to worry as much about tearing up the lawn. This may also allow you to buy a bigger tractor which will make plowing the drive and other chores easier as well as being a better help on the farm down the road that you mention.
2 acre lot will be the main issue right now, with a 120 acre farm as a secondary issue. Just found out that it is exactly 120 acres today because I coincidentally ended up speaking to the farm owner's husband about it on the way to Court regarding what the county gains in property taxes should it be developed versus keeping it in the Farmland Forever program. Anyway, the ultimate goal is for me to buy my own farm in the near future in the 100 to 400 acre range.
Budget right now is about $15,000 to $20,000. I'll probably have around $10,000 to $15,000 in cash for this purchase after tax season. After next tax season, my budget could possibly be around $30,000+, but I don't want to be spending money on a tractor just for the sake of spending money on a tractor and having way more tractor than I will ever need. Don't mind a little more tractor than I will ever need, versus too little tractor in the very near future. I thoroughly believe in using the right tools for the job.
Ultimately, I think I am going to go with the suggestion of two machines. A zero turn mower for the grass and then a CUT for other chores. Plan on putting in a wood burning furnace with natural gas backup and the tractor will also be used for getting firewood when it will be handy to use it. Lots of work to be done. I want to rip out the rear patio and wood deck and replace the patio with pavers and the deck with Trex. Then, I want to rip out the front walkway and asphalt driveway and replace them with pavers. Most of the landscaping around the house is dead, so it needs to be pulled out and replaced. I guess that is what you can expect when buying a foreclosure.
Need to buy a chainsaw and pressure washer too.