"I'm sure I'll be corrected here by a Hobie history buff, but they raised the tramp on rails on the H16 when they realized that they'd but in the water a good deal of time on that boat."
I have no idea how they decided on the raised tramp frame, but the H14 came before the H16. For the H16, it looks like they just scaled up the 14.
There is a school of thought that says be careful how tight you make the tramp. You could stretch it to the point that it will meet in the middle, and you would no longer be able to take away the slack. For that reason, I wouldn't recommend squeezing in the side rails.
I have no idea what a boot hook is, but on my 16 (laces up the middle and across the back), I use two combination wrenches and several pairs of vice grips. Make a "T" with the wrenches, use the open end of the larger one to twist the line. Use the vice grips to hold the line at the grommets as you work your way down. I learned this at Madcatter many moons ago...
No matter what, your back is usually in pain after adjusting a tramp.

Mike