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Well if this isn't a sign from the motorcycle gods I don't know what is. About an hour ago i was looking at pictures of the 06 springer custom that i used to have a few year ago...i really loved that bike and I really started thinking about looking for one again. I almost messed up and said that out loud with wife near by. To answer the op's question I would love to have a choice between two bikes
Have to have 2. The Pro Street is my fun bike with a voided warranty. The Ultra Limited is bone stock, under extended warranty, and is my favorite when the the wife wants to go with me or when it’s cold.
I have 2..... 2003 FatBoy and a 2009 Road King. The Fatty I use for in town riding/bar hopper. The King if for obviously longer rides and 2-up. When I bought the King last year I was convinced I was going to sell the Fatty.....I even had a deal on the table for near what I paid for it......but I decided against it as I can't bring myself to sell it, love that bike.
As mentioned already though.....it is obviously an expense. I do ok for myself but I am in no terms wealthy. One way to save money is to do all of the regular maintenance yourself. Once you invest in the right tools (most of which you already have) it really isn't bad. I can do both bikes for about $120 myself. If you keep up to date with the services you'll be shocked at how many other issues that most of can't (or don't want) to do are avoided. Insurance really isn't too expensive on these as they are older bike too.
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.