Regarding 2: I struggle with this all the time - I always start working on something one way but as soon as I come to a realization that there may be a problem

Regarding 2: I struggle with this all the time - I always start working on something one way but as soon as I come to a realization that there may be a problem with the one, I switch to the other way. It leads to a lot of thrashing. This is never a good approach, fully implement one way and make it easy to swap at a later point and document problems.