1 AM Scheduling Headache Questions

If the sun sets at 5:20pm at the latest on any given shoot night, is 7pm going to be dark enough for shooting night scenes?
Should I actually get a permit for shooting on the sidewalk/street in front of the bar (note: the place is deserted at night)?
Or just stick with shooting handheld and risking it (if a cop shuts us down I’m pretty much screwed)?
Is ten minutes enough time to rig up this one blood effect shot?
Will my DP want an additional twenty minutes that we don’t have to rig some light?
Will anyone cry “mutiny!” and run off my set at 2 AM?
Am I an idiot for sinking several grand into this endeavor?
Am I a good enough filmmaker to even pull this off?

I am hoping the answers are: yes, no, yes, yes, no, no, no (but you’re an idiot for other reasons), yes.