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Sounds like you would be financing around $9K to $10K after the trade, which isn't that bad to get something you really want, and if you can handle the payment without a problem.
I know a couple of guys that own Softail Custom's, and one of them is like the Vivid Black model you are looking at.
Beautiful bikes (especially the Vivid Black model)...
My opinion would be to get a previously owned one. If you decide you dont like it after a year, turn around and sell for close or same as what you paid for it. Reason I say this is I started out on a used Sportster, sold that and got a beautiful used wideglide and eventually sold that and bought a new Electraglide. Kinda like working your way up through the ranks. If you think there is a slight chance you will do same, stick with pre-owned ones.
As far as I'm concerned you selected what I think is the pretties bike that Harley makes.
Regarding the finances. I often think of what a friend of mine said when he bought a near one million dollar home. The price is "only a number"! You figure what the ongoing costs involved are and if you can handle those costs without causing yourself a hardship - do it. I'm sure you will never be sorry.
I too bought a Sportster and loved it, still do. Still have it, but selling it to my son. Took a ride on a Deuce, and knew immediately that the softtail was for me. Bought an '07 and have NEVER regretted it. Funny too, when I get back on the Sportster, my first impression is: What a cute little bike! You'll love it.
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I can think of a lot of bikes I'd rather have in addition to your Sporty for the price differential. But, that's just the way I look at deals like you propose. Sounds like you have some reservations in your own mind or you wouldn't have asked the question to everyone else. Bottom line is that we don't matter--we're not cosigning with you.Be the Man--follow your own heart.
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.