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OP you did ask but when I post a hater or two might show up.
My riding is divided between 24 bikes. Some of every H-D family and some like the 13 Street Bob with a 120R for the pure fun of it and the stage II V Rod.
I tour them all across the North American Continent. The Street 750 did Sturgis on their 75th Aniv. The Sportsters, Dynas and Softails have seen much of the U.S. and Canada.
Most but not all are on my profile page with the link pictures.
Lol. Yeah, that's kinda what I was thinking.
I currently own a Road King as my primary ride and my Snorkster as my fun ride, and my wifes play toy. Kinda like I have 2 Chevy trucks. One for getting to work, and one for pouring endless amounts of money in to, in the pursuit of the "perfect" hot rod. Multiple vehicles is the common place in today's world. Just a fact....
I promise... Deciding whichever bike to ride, was never an earthshattering delima that I was unable to overcome.
Personally it depends on what you can afford.
Afford meaning more than just own.
If they set in the corner or the shed out back and deteriorate, that is not affording.
If you can maintain, ride N enjoy keep buying.
I plan on adding at least one more (just before I retire).
I will add a third if I ever find the right bike for the right price.
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.