My labored decisions were about engine size and drivetrain upgrades to support the increased torque.Met a lot of fine people in the process.It was worth every waking moment.
Get an 09 Road Glide. Then add the tour pac and all the goodies. You will have the best riding Touring Bike Harley makes. And if you ever go to a large parking lot full of harleys, you stand a fair chance of finding the thing without using your GPS. The only bike more common than the Street Glide is the Ultra. But you will have to deal with all the folks that are secretly jealous of the guy riding the RG.
Another advantage is I can carry a 18 pack of bottles in the tour pack and two six packs in each saddlebag (more than a road king can carry, that is unless u buy a tour pack and add it on)