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I was in the same boat as you. With perhaps a lot less $$. I wanted that Street Glide, but loved my Road King. Ended up throwing a Dead Center detachable fairing on, and now I have both. Very pleased. Best of both worlds, although the longer I have it, the less it comes off. I'm almost to the point that I think I could own an Ultra or SG with the fixed fairing. Hope this gives you a little different perspective to your situation.
I am not an expert on anything older but I can give you my take on my '09 street glide.
Things I like:
The new gearing makes it very responsive
The new frame makes it very tight and stable. Have taken many 90-100 mph sweepers no problem
Handles great, feels much lighter than it is. I use it for a daily driver in traffic
Very comfortable
Love the stereo, cruise, and other bells and whistles
The fairing is terrific on cold days
ABS is great
Red Hot Sunglow
Things I changed fast:
Windshield looks great but is a PIA, bought an 8" smoked and fixed that
Seat is fat causing someone vertically challenged (I'm 5'10") to have to tip toe. Bought a C&C fastback and fixed that. Its very comfortable and I can now flat foot with knees bent.
I will be talking to Fuelmoto in Feb to get setup with their stage 1 kit.
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