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I traded in my '03 Heritage on my used '09 Street Glide. I love it! The OL loved the Heritage and says the Fairing is ugly. I think she secretly prefers the SG. Especially now that I've added the detachable tourpak.
Fatty is easier to handle at slower speeds/in town and local rides, but for highway and over night trips the SG gets my vote. I too started out on a Fatboy, and had to adjust to how the SG handles in comparison. If I were to sell the SG, I would look into the Road King Custom, as well as another FB.
I came from an '08 Night Train (not by choice- it was stolen) to a '10 SG. I REALLY miss my Train, but there is ZERO comparison. NONE. I cannot stress how much better the Glide is in almost every category. I can go ALL DAY on the SG- this past summer I did multiple 200mi+ rides without even thinking about it. The cruise control, 6-speed tranny, riding position, hard bags, stereo, handling, etc... I could keep going.
But again, it comes down to what you want/need. No one else can make that decision for you.
Here's a picture of my '08 Fat Boy. Sold it to get a 2013 SG and haven't looked back. I really liked it, but you just can't beat the Harley touring bikes, especially if you are putting serious miles on. I don't think I'll ever ride anything else from here on out. Good luck on your decision.
I've got both. Different bikes for different purposes. Love my FatBoy for around town, SE air cleaner, Rush 2" slip- on's and SE 204 cams.
My Street Glide is basically stock except for the Rush non-cat head pipes, SE air cleaner and Tru-Track stabilizer. For the longer rides the windshield, saddle bags and radio are sure welcome.
I've had 08 Softail Deluxe, 09 Ultra Classic. On a 2012 Customized Street Glide w/detach Tour Pack now. "You ain't riding, unless you're Gliding". I'm just sayin!
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Slideshow: The Swiss custom shop has taken a Harley Softail and stretched it into something so long and low that it looks closer to a rolling sculpture than a conventional motorcycle.
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Slideshow: A standard cruiser becomes an intricate metal canvas in the hands of a Swiss custom house known for pushing Harley-Davidson platforms far beyond their factory brief.