I've had to write myself out of a few corners I've painted myself into, so I've found it's extremely useful to ask those questions before I paint myself into the corner, but strangely enough, I always had fun figuring out how to get out of it, regardless.
Ah, rewrites. Never seems like you have enough of them.
I'll have to start asking those questions to plan out where the story is going long-term... if I decide to go long-term. The advancements in the story have mainly been in response to the prompts from the writing group. I'll have the next one ready soon, but beyond that I'll need to start putting together a storyboard.