The least amount of effort on your part will increase the times you actually go sailing.Do not erect barricades that get in your way.

If you take your boat apart,than you must take time to put it back together.Can you simply back around behind your house and park more parallel to the slope perhaps cut a small area closer to being level or split the difference and end up on a more manageable spot.Maybe get some landscape block and back fill a more level parking lot.You need to be able to back in your back yard,hook up to your boat and go to the lake.Put some thought into making your sailing time simple so you will spend more time sailing and less time trying to go sailing.Maybe park your Hobie in your garage(folding tongue on trailer) and hang the mast from the ceiling diagonally.I am sure your wife won't mind park her car in the driveway

...as long as your boat is safe in the garage.
Bill 404 21SE