I my perfect world of self-hosting, I take all the time I need to implement features and reduce tech dept over very long time spans. Sometimes, a migration from one service to another, or from one type of doing things to another, takes a year or more. During this time, both options run indefinitely alongside each other until I decide that it is time to deprecate something. This is very gratifying. I have reduced tech dept continuously and I see progress. Where I needed 2-4 days per months to manage things, I am down to 1 hour; and this hour is often adding and experimenting with new features.
I say "perfect world" because:
- everything is under my control, I worked hard to reduce my dependencies
- I have only about 10 people to care for, and they largely stay the same
- I have no other goals than time reduction and liberty; both go hand in hand
I am not sure this is possible in companies.