I just went out to start my '08 Street Bob and when I hit the starter, I had smoke coming out from underneath the air cleaner. I shut it off, tried again and it started normally but I had intermittent ignition while going down the street. Any suggestions?

 

smoke was probably a kick back and would be normal for compressed fuel mix to flow out the cleaner.
could be several causes. could be the plugs, wire or ignition module. sometimes when you start a machine, the battery voltage is drawn down low and then surges as it recovers, this could skew the spark, sometimes it will fight the starter and the engine will roll back a tad and cough out the carb. this is a bummer if you only have a manual foot. everytime i started having issue with this, a new battery was looming in the future.
another good sign is the starter bendix will make noise engaging the ring gear.