Re: sailing backwards upwind? oops.
"most travel lifts require entering backward if you don't want to drop your forestay."
Then if you back in, don't you have to drop your backstay?
Forestay, backstay...either way there's a wire pretty much the same size and shape coming out of the mast(s). Maybe a lower angle on the typical backstay, but there's still a stay up there.
When you are engineless and need to maneuver the boat, remember that before there was a starship using warp drives, warping the boat was the normal way to shift it around. Toss out a couple of lines, and manhandle it. No biggie.