[galdosdi]

In my experience the problem isn't really lack of time/resources, but lack of accountability. There's always more to do than there's time and you just have to estimate and prioritize.

But even for cleanup efforts that clearly are worth the time/priority, places that develop these problems really bad usually make it very difficult to be in any way rewarded for thinking ahead to how your technical choices today will impact things in a year or more. People who stay there internalize this lack of accountability and stop trying.

You need your people to feel like caring about and investing in the future is a valued priority. Otherwise, they won't, and then you'll arrive in that future, and it will suck because everyone didn't care to build a good one.