Four winters?! That is wild, because most of the caulk-over jobs I have seen fail within a single season up here. Forty years of old junk coming out of one joint is honestly gross to picture (and I bet it smelled amazing, ha). Ray sounds like the kind of neighbor everyone needs, the ones who just watch you mess up and then drop one line that changes how you do everything. I have to ask though, did the hydraulic cement crack at all after a couple freezes, or did it hold up the whole time?

Ever notice how the best results usually come from doing less? Same thing happens with steak, people flip it a hundred times when you really just leave it alone, and bread dough gets better when you stop messing with it. So yeah, letting the pour over drain on its own makes sense, sometimes your hands are the problem.