JMHO....but:
as far as the philosophy "I don't wear gear if I'm just coolin' it, or just going for a short hop".
3/4 of MC accidents are caused by other vehicles, and occur within a mile or so of home. 2/3 of those accidents occur within 10 minutes of the beginning of the trip.
http://www.clarity.net/~adam/hurt-report.html
If I knew when I was gonna be in an accident, THAT'S when I would wear my gear.....unfortunately.......
If you read the results of the report carefully, you may conclude that the shorter the ride with the more intersections and the lower the speeds, the more likely the case you would need your gear.......
.....and you'd be right.