Joe,
I have a similar problem with my '06 Classic. When I stop at a light and put it in neutral it sometimes will not engage first or will slip out of 1st halfway through the intersection. I complained to dealer at the 500 mile service (Baltimore) and they said they have heard complaints about it and that it should get better after some more miles. I did adjust the clutch using the lever adjuster and it improved significantly.
I had a couple of close calls with it. On the last club ride it popped out as I was pulling onto a busy road out of our Triumph dealership, I tried shifting into second quickly but ended up stalling it none the less... not enough twisting on go handle I guess, imagine that... The four wheelers where kind enough to go around.
I filed a complaint at the safety web site as I don't think it should do this at all. The safety site looks for trends and will also send a copy of the report to manufacturer and to the service dealer. If you get a few minutes you might fill out the safety report. The web site is
http://www-odi.nhtsa.dot.gov/ivoq/
Brian