Mine always fires right up, Just turn on the switch, wait until the fuel pump quits running and start. It turns over about two times and it's running.
It sounds to me like there is something wrong with the setup on yours.
Hopefully the ECM update will fix it. Other than that I would start thinking about having another dealer look at it, because yours is NOT acting normal!
Good luck!

 

The only time my 550 did not start the first time it was sitting outside in -32 F with a wind chill of -59 F. I read the owners manual cold weather starting procedure. It say to turn the key to the on position wait 10sec then turn off wait 5sec Repeat twice more. This works when it cold.

 

Mine has always started with no problems but I checked the battery cables and the + side was loose,you may want to check yours, a bad ground or loose wire can keep you trouble shooting for hours. Good luck