I have had 4 motorcycles made by HD. My old ironhead sportster was unreliable, but that isn't a fair comparison because it was so old, and that was the source of the unreliability.
My '06 Roadking was a horrible bike. First it ran HOT and surged and popped. Then I put in a PCIII into it to deal with the lean condition. It ran way better but the fuel economy went WAY down. It was inpossible to find neutral when it got hot, and the steering head bearings got loose. The paint started cracking around the tail light and slight rust stains started to show in the white paint. I couldn't wait to get rid of it.
My '05 Sportster was a great bike though. It was solid and reliable right from the start. Even as an 883 it had enough power to beat nearly any regular car off the line. It was surprisingly good on the highway, but it didn't have a lot of reserve power for passing. When I did a 1200 conversion, it was better in all areas though. Even with all the performance upgrades I did, it still got around 50 MPG. I don't have a bad thing to say about that motorcycle.
My Buell Cyclone has been every bit as good as the Sportster as far as reliability goes. It was worlds different in power and handling though.
I would recommend a Sportster to anyone who wanted a simple, non-nonsense motorcycle that isn't pretending to be anything it isn't. As far as functionality, I like the Roadster versions. If I were you, I would look for a 1200R that is a 2004 or later. That gets you the rubber mounted engine. I think 2007 they got EFI, but I'm not sure abot the year on that.
Great motorcycles from my limited experience.
Good luck!
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