skyhook?

Sounds like a hastle and there is potential for damaging the boat. Know anyone with an empty lift? Dump the boat in the water a buy them a case of beer for the use of their lift

My boat isn't that big in perspective (21' approx 1000lb dry), but I tied the back of mine to a large palm tree in my front yard, unhitched the front then slowly rove the trailer out from underneath. I threw a few old tyres under the back and front as I went.
Getting back on is a little trickier but I basically hooked up the winch strap, spray carpet on skids with mr sheen, then winch and back the trailer back under slowly at same time.

Do a search, there are several posts on this in the past.

You can also go to a marina and they will pick it off and store it for you. Extra money but if you don't have the skills beatins tearing up boat

fork lift and a frame for stern for the freeze frame boat

Why not find a well and just put the boat in the water ?

Go to a marina and have them set it in dry stack for a couple weeks. Cost is probably less than what your time is worth to get it off and on in your garage.

Roller trailer? Put a snatch block on the fwd crossmember, run the winch cable through the pulley & back up to the bow eye. Winch the damn thing off quicker than running to the marina. When you have weight on the stern blocks, start moving the trailer, not the boat.

Its not a major deal....

Yard arm that I borrowed but man it was nerve racking the first time!!!