I think 1000 miles is right around when it for me it stopped being some big event for me to take the motorcycle out anywhere. Those first few hundred miles every time I got on the bike I'd have to give myself a pep talk, be mentally prepared, I'd have a healthy dose of fear/stress/amazement while riding, and inevitably I'd make a mistake or two per ride.I think 1000 miles is a pretty big turning point for most. Somewhere around 750 miles a light bulb went on over my head and I started doing alot more things right. Not really scared of it much any more. It's a very stable and predictable device if used within it's limits (and mine). About the only thing that freaks me out is wind like you get if a storm is approaching. Unpredictable pushes this way and that at highway speeds can be very disconcerting.
After about 1000 miles, while there is still obviously a lot of learn, I don't think twice about taking the bike anywhere - I've frequently used it for commuting in rush hour traffic.
My point is I think we've all been there, and you do reach eventually reach a point where you get more comfortable with things.