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Look at the signature pic for a fellow here by the name of "baka1969". I'm surprised he hasn't chimed in here yet. I think he packs more stuff then half the bagger guys do!
I'm never going to suggest overloading your equipment, but I've had probably 40# on the same rack many times on sportsters, with great success. Duffels work fine, but purpose-built motorcycle bags just do the job so much easier. I chose Iron Rider bags for their ease of use, and have had the same bags on two sportsters, a road king, and now my Dyna Switchback. One smaller bag if I'm solo, A big one with the smaller one strapped to the top of it if the wife is with me.
There are tons of bags you can get. Built in lashing straps, a rigid bottom to keep shape on the rack/seat, and custom rain covers make them worth the money. $100 on my main bag, and it's been great for about 7 years, and still works like new.
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.
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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.
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.