It seems I have seen some hitches made for equipment towing behind vehicles, for making moves easier between farms. If you can stage several pieces of equipment at a place, then move a tractor there to use with them with the last one, you might haul all the implements quickly, and then only need one "deadhead" ride to get home from moving the tractor over, and then go back on the truck.
You may have a retired friend, who'd be glad to help you move every so often. Every car dealer I know has a couple of older guys who still drive well, who simply ferry vehicles between dealerships.
If you haven't already got that tow-truck set up for repairs, having at least a few basic tools and supplies in it will save you a lot of lost time running back to the shop. Throw in a good first aid kit, too. Can't hurt, and might help.
I am a huge fan of the check-in. If one of us is overdue getting in from the afarm or anywhere else, the other one expects a call as a courtesy. In truth, having someone who knows your schedule and location is a safety practice. We text a lot now, since that takes less signal to get through, and the message is right there on the screen, instead of having to call voicemail for messages.
This is really a logistics problem for the most part. Like some have said, sticking to land not too far away from the farm is probably sensible.
