My factory radio comes on when I turn on the key, but doesn't always come back on after I start the truck. If it doesn't, I have to turn the truck off, remove the key, wait 10-15 seconds, and start over. Ideas?

There happens to be a technical service bulletin aimed directly at that very issue.
SYMPTOM/CONDITION:
No radio audio or display following engine crank. All radio functions return when ignition key is turned off and back into accessory.
Bulletin NUMBER: 08-018-06
Contact your local Chrysler/Dodge dealer service department to discuss having this software updated.

Your radio may be a symptom of a anti theft system failing and not checked could eventually leave you stranded unable to start your car.