Thanks for your kind comments, and added info. Given your need for frequent trips to your cabin I believe that the suggestion to add a 50 AMP circuit to your cabin is the best solution, but I'd suggest either a 40AMP or 60AMP circuit instead. Here's why: The SR+ onboard charger is limited to 7.7KWH speed - which would be a 40 AMP circuit - that should be even a bit less expensive than the 50 AMP circuit (smaller wire) to install.
I installed a ClipperCreek 40AMP charger in my home to power my Nissan Leaf and BMW i3. It works fine with the Tesla M3 using the supplied J1722 adaptor that comes with the car. If you might buy the Model Y you may want to spend a bit more and install the Tesla charger with a 60 AMP circuit. Both the LR and Model Y can use that full power - the SR can't because of the slower onboard charger.
My M3 LR charges at 31 miles/hour using the ClipperCreek - more than enough for my needs, and your car should charge at a similar rate, even with the 7.7KWH onboard charger. Frankly 25-30 miles/hour range on a 40 AMP circuit is fine for pretty much anything. An overnight charge should easily get you to your SuperCharger without concern. Even with my LR I don't see the need to upgrade to a 60 AMP circuit and 44 miles/hour range pickup.
This is the link for the ClipperCreek charger:
Buyer's Guide to Home EV Charging Stations
The HSC40 model should be fine for your needs. It connects directly to the charger, no need to add a separate plug connector. It's the model I bought. Works fine. It's $565. Adding an electrician to do the wiring (plan carefully - run as short a wire as you can to the EVSE to minimize costs - my connector is only 5 feet from my electric service box - install was under $500). Including the ClipperCreek charger the entire install was roughly $1000.
You'll likely get 25/miles of range/hour with a 40AMP ClipperCreek (or other brand) charger and your SR onboard charger. You also won't need any additional adapters, keeping your costs very reasonable. Compared to a $10K hit on resale, installing a charger at the cabin seems like a good option for you.