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?
Now, ask them to paint a mural instead. The estimates will change, they'll probably give you a broader range instead of being able to estimate almost down to the minute (and being off by no more than an hour or two) like someone just painting walls (with a known environment, surface type, and paint material).
Does the mural need to be designed? Are the desired qualities of the mural well-specified or will there be a series of back and forths? Maybe a set of prototypes (sketches) so that you can refine your requirements. At that point, the estimate for the total task (design and paint a mural, or design and develop a software application) becomes far less clear.
There are certainly programming tasks which are closer to the paint-a-wall task which are much easier to estimate reliably, but they're far from the only thing people in this field work on.