I think it’s reasonably easy to design a system that’s documentable and documented. It’s very, very hard to maintain and iterate on a system while maintaining those properties.

Hacky things will make their way in because it takes a month to do the documentable thing and a week to ship the hacky thing.

It takes a lot of skilled people from varying disciplines to figure out what things are going to survive long enough and be important enough to spend the resources doing the right thing instead of the hacks.

It bites both ways. I’ve seen core business products crippled by years of digital duct tape, but I’ve also seen internal tooling that never really becomes useful because they insist on doing the “correct” thing and it’s constantly a year behind what we need it to do.