[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.