The "did we all just get softer about chasing people down" part hits hard. I think a lot of it is that nobody wants to be the bad guy anymore, so instead of saying hey I can't pay this right now, they just disappear and hope you let it go. Three years ago people felt some shame about an unpaid bill. Now it's like a shrug. The phone makes it too easy to just never answer.

Oh man, I read a small biz blog once that said most people wait way too long to get firm and it almost never hurts the relationship once the money shows up. Good on you for finally sending it.

My buddy Dave did the category limit thing for like a year and swore by it. Then his kid needed a new laptop and he went to check his "fun money" and realized he'd been double counting his coffee runs into both his food budget and his fun budget the whole time. So his limits looked fine on paper but he was actually about 90 bucks over every month and never noticed. He switched to tracking every single charge after that and found a bunch of little stuff, mostly app subs and vending machine runs at work. Idk man, limits are nice in theory but they let you lie to yourself. Seeing the actual charges is what makes it real.