Simple answer. ROAD KING! Why do you think it's called the KING? You'll never regret that purchase, and if by some chance you do, well....YOU WON"T!! Good luck
You have to get what you really want, or you will be sorry later!
No doubt! That's what's got me in knots . . . I talk myself into the Road King, no fooling, then I go into the dealer and see that Fat Boy . . . it's a lot of money for buyer's remorse, or as isac said, end up upgrading in a couple of years!
All I can say is my buddy had a fatboy (his first harley) and he had it for about 3 years and traded it up for a touring type. (classic). He liked both but says he wouldn't go back to the fatboy now that he is doing longer distances and is riding with somebody. Roadking all the way (and I had one of these before a Street GLide). Besides, with the king you have bags and a more solid feeling bike. Much better for traveling, especially with a mate.