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Attend or search for a HD store where they provide a test ride day where you can ride what bikes they have and see the difference likes an dislikes.
I have been well please since 09 adding what I want put on my bike and it has been a true pleasure 40,000 and growing.
Yeah... What they said. All the Touring models are great. I have owned the Road King and now an EG Classic.
Get something with a touring seat, tour pack, and fairing for long haul two up trips. You won't be sorry and if you don't get all that and you really do take long trips two up, then you will bare the expense of adding it all later.
All the fairings are great as long as you get an aftermarket windshield that fits you. Look at Klockwerks and Clearview Recurve. Both are great and let you see over the screen without getting your head buffeted.
If you're like me you won't mind getting rid of the little haywagon at all. I had a wide glide as a second bike to scoot around on and even though it fit me well ergonomically, it rode like heck. Got a good trade in amount for it on a '11Road King and couldn't believe the difference. Like others have said sooner or later you'll step up but ride some of the various touring models first.
I say any of the touring models will be a good move for 2 up riding, but the street glide would be my last choice unless you want to spend a couple grand to make it the way you really want it for two up touring.
You'll have to replace the stock windshield, seat and shocks to be as comfortable as any of the other touring bikes. Then you'll still have to add a passenger backrest, luggage rack and T-bag or tourpack to get the same storage.
I really like my SG, but I could've saved money by just getting the ultra to start with and I still don't have a tourpack yet.
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