Wow, Karl, that's much better than my Hobie 20, 16, and Laser all in a low-ceiling two car 19x20 garage! Our cars have to sit outside, too :-( No way a 30'+ mast fits in 19x20 though; do the simple A sq + B sq =C sq triangle math. I've also found that a lot of 19x20 standard garages are only 19 deep; that would be a challenge.

The trailer is the key; my sailbox and rear cradles hit the back wall and the tip of the tongue clears the garage door lip by less than 2". I put a pair of rollers on a 2x4 and hang it off the trailer winch; as I pull the 20 forward on the trailer this supports some of the weight (the 20 has LONG bows). That 2x4 also comes in very handy for installing the hull covers single-handed (lift up the bows and slide the covers over the cradles). The 16 has plenty of support when slid forward and doesn't need the 2x4.

I also knew of someone who lifted the tongue of the trailer up in the air; this also reduces the overall length of the rig. Make sure you chock the wheels; this guy had the boat in nose first, tilted up, and all ready to take off down a STEEP driveway :-) Pretty scary looking.

The Laser rides on a custom wood cradle on the 16, and travels to winter frostbite races that way. To get the 16 all the way in the garage, AND to have a central walkway, I have to put a floor jack under the axle and scoot it sideways over to the wall. That IS a PITA, but every time I have to do it, I keep saying "$800 a year storage, $800 a year..."