Check the fuel pressure. If that's good, then check the output on the engine temp sensor. If that's fine, look at the plugs. If they show fouling, replace them. I don't think that is the issue, but it would be a shame to spend a lot of time on it only to find that it was fouled plugs later. Also voltage drop the starter while you crank it, make sure its not dropping below specs.
If all of the above is good, and by that I mean you checked it all with gauges and meters, then its time to work on the tune. Initial fuel pulse and cranking fuel.
The first step in checking Harley codes is to purchase the electrical diagnostic manual.
The second step is to clear the codes and then see what comes back after a 20 min ride.
Codes pointing to a bad part is a myth. Codes direct you to a diagnostic procedure.
temp sensor would make sense, since it starts up cold every time.
plugs should be fine they have less than 4k on then , I swapped them before the tune which I had done after swapping the cams , lifters and rods ( did that myself .. tune was done by small Harley shop )
the fuel pressure is something I can start taking a look at
not sure what the voltage drop test is. do you mean measure the voltage when cranking and making sure it doesn't drop too low?
Think my plan will be to ride a few times since I cleared the codes then try to reproduce the issue to see the new error codes and start from there.