I don’t know. I think that’s the main truth about software engineering. Maybe an open source version of that Streak app exists and OP is re-inventing the wheel. I think the brain doesn’t like task list. It may be pleasant to do, but most of entrepreneurship or coding is exploring. And a task list blocks you from exploring.
I'm curious: if you hired a contractor to, I dunno, paint your walls, would you accept "I don't know" as a time frame or price quote? If not, what's different about software development that makes "I don't know" a reasonable answer in our profession?
The seemingly infinite amount of variations in software tasks and the ambiguity of the requirements? If my job involved only putting up or modifying API endpoints that involved querying a single SQL database, I'd get quite good at that and be able to tell you with very good accuracy how long an endpoint would take to put up.
Just as if I painted many walls before, I could reasonably tell you how long painting a wall would take based on the surface area, height, and amount of non-wall obstructions. Also, contractors tend to be their own salesmen, so just because they speak confidently, doesn't mean they are. It's not like contractors are universally famous for being on-time and underbudget.