I used to hang my H-17 from the garage ceiling and store the trailer beside the garage in the winter. In the summer, the boat was still hoisted, with the trailer under the boat pushed all the way back in the garage, because my garage isn't long enough to hold the boat on the trailer.
With the boat on the trailer, hoisting them both, you'll need a good mechanical advantage system. I don't remember what I used for just the boat, maybe a 2:1 block arrangement at all 4 corners. While I could lift the entire boat at once, it was easier to lift the front, then the back.
You'll probably want a 4:1 or even a 6:1. Make sure there's clearance for the garage door.
You could use an electric winch too.
Another idea that occurs to me, is something like a dry land boat lift, so you are lifting it up instead of hoisting it.

My brother in law has a barn and stores stuff in the upper level. He bought a cheap harbor freight winch and built a platform to place his stuff on, then hoists the whole works up and unloads it. In your case place the boat on the platform the hoist the whole works up with the hobie on the platform. Might be quicker to load/unload and you my use the boat more.
I made a manual block and tackle system with slings to hoist our kayaks up to the cieling for winter storage. It was such a pain to get the boats up there I only used it once. Whatever you do it needs to be simple fast and easy, if it's a pain, you won't use it very much. I found that out the hard way.
Bob

Keep the Hobie!! rent storage? or hang it like you said,
Do it like a teeter totter on the playground, but with the pivot on one end, pull it up the angle then hoist the low end up.
It would take some engineering but I could see it working.

Awesome. I need a heavy duty version of that which can lift a trailer too. And some failsafes to keep it from dropping on by boat

Make sure the screw eyes supporting the blocks are screwed into the center of the joists / trusses. A 2 x 4 member extending from the joist / truss to the rafters would help distribute the load, as would a 2x6 attached across several joists / trusses in the vicinity of the screw eye.

I've thought about fail-safes for the boat - lines looped around the truss in case the eye ever decides to pull out, but haven't gotten around to it in 20 years of use.

The other thing that's a bit scary is the winch has a ratchet going up, but nothing coming down. If you let go of the handle when lowering, you (and your boat) are in for a world of hurt.