From your description, it sounds like you are talking about one of the spark plug tower drain holes. Are you sure this is gas? If so, that would mean the spark plug would have to be loose and your mixture so rich it was pushing that much fuel thru the spark plug hole. Since you had an uneventful trip of 250 miles, this doesn't sound too plausible.
As for cold starting, not all bikes seem to react the same - part of it could be due to climate.
Here's what works for mine in all but the hottest weather (>100*F):
Full choke, no throttle, then as soon as she lights off (cranking time varies due to air temp, colder takes longer), reduce choke to keep idle @ 2000 RPM. Put in my earplugs, don my helmet & gloves (reducing choke some more may be necessary during this), then get on and go. After ~1/4 mile, turn choke off if it hasn't made it that far yet.