For a first Harley I'd be looking at the Dynas Hooper -- they are great bikes for distance, have the low balance that the more dynamic bikes have (Sporters have a really high center of gravity -- even tho they weigh less this does not make them any easier to handle btw) and ride really smoothly.
No, they dont have the flash of a Deuce or a FatBoy, but there's this thing in bikes called trade ins, just like in cars
If you're really set on getting a Softail right out of the gate, I'd have a close look at the Springer, especially the Heritage edition if there are still any available...