Definitely recommend driveway sensors on the access points. I have the Mule buried sensors on my drive. Doesn't get triggered by wildlife like the motion sensing ones do - has to be something w/ metal in it to trigger it.
If you don't need the tractor for anything else, you might come out cheaper overall if you sell that lift and buy a spider lift. Self propelled on tracks and is great if you have uneven terrain.
Let the swale do the work of starting the drying. Here in NC we just had the second wettest winter on record (just 0.03" shy of a new record). Things are finally drying out around here. Depending on where in eastern NC you are, you may also be dealing with clay near the surface. The...