In a sense you're overthinking it, yes.
The Blaylock EZ Jack and Wheel Chock for Tandem-Axle Trailers # EZ-JACK can be used both to help level out your trailer on uneven ground but it's also great for temporarily raising a side of the trailer to change out a tire like what you mentioned doing. You just want to avoid leaving your trailer in that position for an extended period of time at full capacity.
If you do need to leave your trailer jacked up like that for a while then you need to... view full answer...
To easily fit the center portion of the Epicord Battery Disconnect Switch # 277-000096 through your wall you'd want to drill a 2-3/4 inch hole so that would be the size hole saw to use. view full answer...