I've owned a couple of sportsters. Probably some of the most uncomfortable bikes I have ridden. I'm only 5'9" and it was too cramped for me and the ride was too rough for my taste. My wife rides one but she is tougher than me I guess.
If its for looks and shorter distances, I say go for it.
If you really want to rack up the miles and enjoy the ride, I'd look elsewhere.
I know it's slightly put of your budget, but a brand new Dyna Street Bob is only about $12,500 brand new. I've seen plenty of used ones in your price range.
Oh, and unless your significant other is built like a 12 year old girl, riding two up probably won't be much fun for either of you.



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