I'd say it depends on how much effort it'll take to deliver the work. Want to spend a day clearing up a piece of technical debt? Guesstimate how much faster you

I'd say it depends on how much effort it'll take to deliver the work. Want to spend a day clearing up a piece of technical debt? Guesstimate how much faster you'll end up adding new features after resolving it. But the bigger the piece of work the more effort you should put in quantifying it.