I have a chance to pick up a x roads with hard bags for a very good price.
I'm sure it's a killer deal.
Is the older trans that big an issue that I'd be kicking myself.
No, it's not even an issue. But being the picky princesses that we are, some of us (including me) like to complain about anything and everything - too much gear noise, not enough exhaust noise, too much wind in my face, not enough wind in my armpits, etc.
My other choice is an 11 Kingpin.
They're two different animals. I have also considered both and since I take my wife along sometimes on longer trips, I went with the touring bike (XR). But if you ask me the Kingpin was the better looking bike of the two. I've now gotten so used to having the hard saddlebags, that I don't think I can ever go back to a cruiser without lockable bags.
In my opinion, the XR will be the better touring cruiser, and the Kinpin will be the better looking cruiser, even though both can tour and both are good looking.
If you're going to add after market stuff, there's more stuff available for the 'pin since it's been out longer - and less goodies are available for the cross bikes, since they're still relatively new models.
Test ride both and don't stress too much about it - one is the better fit for you, but neither bike is the wrong choice.