I think there's a fundamental problem with trying to logically rationalize stopping drinking by looking for answers to questions like these, certainly before you've stopped drinking for a good while and seen how things are on the other side. Weighing things in the balance, developing a warm cozy feeling about quitting, how great it will be, what you'll do in this or that situation, having everything lined up, etc., just doesn't ever work in my experience - quitting just plain sucks at first, if you're an addict, and there's no way around that reality. We cannot think our way out of a drinking problem, because that very same drinking problem clouds our rational logical thoughts that would otherwise let us see how illogical it is to think our way out of addiction. The one and only way out is to stop, not tomorrow or next week but now.
For people with a minimal drinking problem, perhaps it makes more sense, but the same reality applies: You won't know what is and isn't a real issue until you quit and stick with it for a while. Otherwise, it sounds a lot like rationalizing continuing to drink, by waiting until you have all those answers in hand before you stop. You might wind up waiting until you die.