Man, I feel this in my soul. I spent a whole season fighting that exact same battle, slick cord sliding through the toggle every single time, and I kept blaming my throw when the gear was the problem the whole time. The milk jug in the backyard thing is genius too, way better than driving two hours just to watch a rock bag fall down again. Dave owes you an apology after all that roasting, honestly. Thin high branches are the worst, have you tried just hanging the line way out past the branch and walking it back into place instead of trying to thread it clean?

Plunger from the grocery store did the same for my tub, fancy ones just break faster.

Ha, I love this but I gotta push back on one thing. Those cassette adapters are still being made, you can get a new one on Amazon for like 8 bucks, it's not a dead format at all. The used ones on eBay asking 30 are just people hoping nobody checks. I ran one in my old truck for years until the tape deck finally ate it. The CD thing I totally get though, 47 discs that all still work is a better track record than any phone I've ever owned.