To me, the problem in choosing the "better" way of doing something is that I can't stop comparing diverging design choices.

I like to think that the best way to choose between seemingly equally advantageous designs is to start with the one whose first step(s) is(are) the most straightforward. The thing is, while I prepare myself for implementation of that first step, I've a background loop in my mind that constantly checks against other implementations choices. What I am losing here, what I would gain otherwise.

In the end, I never really make definitive decision before starting. I start with that background brain noise on the “most simple first step design”, and when the background noise stops and the raw pleasure of coding kicks in, I known I'm on a good track.