2016 Street Bob. Weirdest thing I've ever seen. I turn on the main switch and then turn the kill switch from off to on, starter won't turn and the entire left side doesn't work. If I cycle the main switch a couple of times the issue goes away. Then the bike starts but only stays running momentarily and shuts down.. That happens 3-4 times and then it starts and stays running. This has happened about 3 times in the past two days. Any suggestions what should be looked at?

 

Intermittent electrical problems are no fun, but start with the basics. Check that the battery and ground cable connections are tight and clean. If playing around with the ignition switch makes it work sometimes and sometimes it won't, you may have a problem with the switch.
When you say the left side is out, do you mean just the turn signals?

 

I would start at the main switch and work back. Especially since toggling the switch seems to get it to fire, only if for a minute before it shuts off.

 

Every function assigned to the left side doesn't work., Hi-beams, horn, trip, and turn single.

 

Just tried to start the bike and I just got a V INERR when I cycled the kill switch from off to on. I'll put the battery on the tender over night and see how that goes.

 

Charging the battery didn't help. I disconnected the neg terminal for about 15 minutes and reconnected it. Still the same.

 

Intermittent electrical issues are typically (repeat..., typically)

Loose or corroded connectors / connections
Bad battery/ weak cell
Loose or corroded grounds
Bare wire intermittently shorting out

Get a VOM - start at the battery connection - measure voltage / voltage drops - track back to / through the switches - back to the indicators / failing part

Double / even triple check...., clean..., tighten - all grounds

Ghost

 

I noticed a change when I touched the controller module. I disconnected the battery and removed and seated the cables, then reinstalled the battery cables. Problem disappeared for now. It's been about an hour and everything seems normal. Time will tell on this one.

 

Just went for a ride to the hardware store for a unrelated issue. Parked and when inside to do my transaction. Came back outside and the problem came back. First no left controls at all, the starter could crank but would only stay running for 2 seconds. Cycled the ignition switch several times and the run/off until I could hear the fuel pump. After about a minute the left side came up but the engine still wouldn't not stay running. Another minute went by and everything was fine. Drove home with no issues.

 

Maybe damaged wires between your controls and further down? Like the handlebars got changed or something and some wires got pinched and eventually started to wear away.

Start with the grounds, a loose ground can cause all sorts of weirdness. I once had a car no longer start after grounding a new stereo to a factory ground location on the firewall. Be sure to check the fitting at the end of the wire too, if you can see any wires around it they can get corroded on the inside and stop working. If nothing else wire brush them up a bit to make sure everythings good with them before you get too into chasing everything else.