[paulryanrogers]

This is ideal. At times though there will be pushback by engineers and product teams drunk on the high of delivering fast and often.

It also requires knowing the approximate amount of debt that may be involved in any given work. Or else actual work may far exceed estimates so often they become meaningless.

[falcolas]

Both of these concerns are a part of maturing as a software developer. Managing expectations, leading your team, estimating - these are soft skills required by a senior or above software engineer.

Estimates, as a rule, are never terribly accurate in the first place, often because of tech debt - adding in cleanup won't make them much better or worse. To give any kind of estimate in the first place, you need to be fairly familiar with the code, which includes the crufty bits that count as tech debt.