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Bought my first sportster (1200C) this year, it my first Harley too. I love riding that bike. I don't think I'll every part with it just add another bike like a RK or FatBoy someday.
I also went thru many metrics over the years. My plan was to get a H-D when I retired.
The thought was that working full time job, part time jobs and side work, raising a family and going to night school did not leave enough time to enjoy a more expensive bike. To that end I bought inexpensive small and midsized metrics. I considered them "throw away bikes".
My favorite bike is the Sportster. They consist of a 03 883R, 09 XR1200, 14 XL1200T, 16 Roadster and I consider the 08 Buell Uly their cousin.
I did have a 11 XL1200C which I toured. Since I tour them often I did trade the 11 in on the XL1200T when they came out.
Here is a shot of the 11 loaded up to go to Sturgis a few years back.