Lots of good advice here so I can't add much but extra encouragement. I agree that you probably should stay away from the antiques and get something more modern (70's and 80's at the oldest). Garden tractors are nice (fun too) but too small to be very versatile and parts are getting harder to find. One exception might be the very big selling brands, like Cub Cadet, at least right now. Remember they aren't making them any more either. The fellow with the WD has the equipment he needs, but try to find a snap coupler blade in your area now. Stay with a standard 3 pt. hitch. We had a WD back on the farm and it was just a plowing (3x14" snap coupler) and towing tractor. For three point work we used a Fordson Dexta and a Commander 6000. My brother had a Ford 4000 and it was a very nice machine and would be very usable for you today. For loader work minimum is power steering, 4WD would be great too.
Personally I'm about to go with a modern SCUT/CUT to use for light loader work and to use to clean out our barn and load manure. Have a Ford 8N and 9N for bigger work like pulling a manure spreader, blading, running a 6' bush hog, etc. Would not expect to move round bales or mount a loader on either of the Ns. Don't have any plowing or tilling "real" farm work to do but I do have an old 2 btm. Dearborn plow to use if I needed it. You might be asking one tractor to do the role that two would be better at. Maybe an older one that doesn't get used as much and a more modern one that can handle the more day to day chores. Depends on your financial situation.
There are lots of what I would call mid size and compacts that might fit some of your needs out there for sale. Actually I'm a bit surprised by the size range of what they call "compact" these days. Good luck and let us know what you decide to do.
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