I am in Southern IL and when its 40+ out I am still willing to drive it for putting around town.  I have found when its cold like this (below 50) I have a hard time getting it started.

I literally have to have the choke fully out, run the starter for about 20 motor turnovers (estimating based on duration), and I have to pull the throttle a little too or it dies immediately after it starts to run.  Once its warm I can cut the motor and it starts right back up, even after running into a store for 10-15 mins.  

Question is if this is normal and expected behavior?  

I have the Raptor Petcock, upgraded the main jet one step, and have the carb screw turned out 1 rotation.  I do have a K&N stock replacement air filter and HD Dyna muffler.

Trailer the bike down to Mike's Motorcycles in Miami. Let it sit in his parking lot overnight. In the morning crank it up.  

My bike had a similar problem when I'd gone up one size on the pilot jet (from 52.5 to 55). Put the 52.5 jet back in and the problem went away (although the backfiring returned). It would be interesting to see if the problem goes away, in cold weather, if you return the main jet to stock.