> I'm making other choices in response that I fear someone will regret in 15 more years.

Junior dev made to maintain some code base: "wtf, all this old code suck. People were really bad at their job".

Same dev 5 years later: "wellll, this looks bad but there must be a reason.". Usually the reason is someone sold a new feature without asking the implementers or even checking what the impacts could be. So it has to be ready yesterday and you'll never get approval to refactor or clean-up anything, until it breaks.