I like the upright storage rig, but go easy on the bow handle - it was never designed to carry the full weight of the hull. I know you are reluctant to make more holes in the hull, but you will lighten the boat much faster if you add a 4" port on the aft deck centered about 2" forward of the hull/deck trim. This will allow air to flow through the hull and carry away the moisture faster. Right now you are just blowing air into the hull and actually risk straining the hull if the air has no way to exit. Installing a 4" deck port will be easy in the upright storage mode. You should be able to trim up to 50+ lbs off the hull weight. Then do a leak test to find out where the water is getting in and fix the leaks. Good project. Good luck with it.
Alan Glos
Caznovia, NY