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I agree with Prot, you can get a really good deal on used bikes right now. A new softail goes for around 20 grand, you can get a mint older one for less than 10 grand with low miles, that leaves about 10 grand to build the bike you really want.
I'd agree with some of the others that you can find a nice used bike from someone who thought they'd like riding and never did. So many stories on these forums lately about finding a used bike with 300 miles on it!
I bought my '15 Heritage in April of '15. If I'd have waited 6 or 7 months, I could have gotten cruise, the newer HO engine, ABS standard, plus saved about $1000 off MSRP. However, I would have missed those 7 months... No regrets!
No point in waiting. I've got a 15 street bob I bought a few months ago and wouldn't regret a thing. If they upgrade the motor your only looking at the 103ho. You can make the normal 103 push more than that easily if you want. Don't wait. Ride now. Jmo
7 Surprising Harley-Davidson Products that Are Not Motorcycles
Slideshow: The bar-and-shield logo shows up on far more than motorcycles, some of the company's most unexpected products have nothing to do with riding.
Slideshow: From the troubled AMF years to modern misfires, these bikes earned reputations for reliability issues, questionable engineering, or disappointing performance.
Crazy Bunderbike Build Looks Amazing, But Is It Impossible to Ride?
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.
Engraved Rebellion: Inside Bundnerbike's Glam Rock II
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.
Slideshow: Harley-Davidson's challenges aren't abstract; they show up in dropping shipments, shrinking dealer traffic, and strategic decisions that aren't yet translating into growth.