If you tie the rudders up properly (i.e., solid and tight) there's no issue with wear on the hulls or rudders. Tie the tiller arms tight so the rudders can't bounce or move around at all. The worst that will happen is you'll have to replace the rudder pin bushings every couple years, but that's a lot better than messing around with installing and removing the whole system each time you sail. If you had a nice set of EPO or racing rudders on the boat, it might be a different story, but for an old boat with plastic rudders, just leave 'em on.
What about replacing the ends with just these???
Those are adjustable tiller end caps. They allow you to adjust the rudder toe-in. They are not intended to be removed everytime you sail.
If you really wan to take the rudders off each time you trailer, the H20 system is the easiest, but it will cost you some coin and really isn't worth the expense on an old boat.