The first bike I owned along with my older brother was a 1964 Honda CB 160 twin carb. I was in my senior year of H.S. in the Baltimore, Md. area and we shared the bike but my brother already had his driver license, so I rode the bike much more than he did. Back then you only had to be 16 in Md. to ride a bike and didn't need a license. Although I was 17 then, my father would not put me on his insurance policy so I did not get my license until I was 18. I got that old parent line, "your brother will drive you wherever you need to go. Sucks being the younger brother. I rode the hell out of that bike. The Baltimore suburbs back then had great riding areas with foothills and winding roads. I turned the bike into a motocross bike and rode it on a railroad right of way that local bikers made into a track, that was in the Sudbury Park suburb. We also rode along a electrical high power line right of way near the Liberty Dam area. In 1965 I graduated H.S. went to Univ. of Md. for 1/2 of the freshman year, then quit to join the Army Jul.1966 for 3 years and spent the entire time in Vietnam, Dec.1966 to Mar.1969, except for the 8 weeks of Basic and 8 weeks of AIT. After the initial year, I extended my tour 3 times at 6 month intervals but on the last extension Congress passed the 5 month early out so I only spent 2 years and 2 full months in country. Sorry for the long bio, but I told you that because while I was on my last tour, my brother sold the bike for a down payment on a new 1968 Mustang convertible, without telling me and wouldn't let me drive it when I got home. Older brothers, huh.. Those experiences on the Honda are what started my love for bikes.
But to get to the OP, the bike I wished I could have kept was my 2003 100th Anniv. Red Road King, my first Harley. I did what most guys probably do and Chromed almost everything that wasn't red. I rode that bike as much as I could to work, charity runs and M&Gs with friends. In 2004 went to Daytona for a week. From 2005 to 2013 anywhere from 4 to 8 of my riding buddies went to Myrtle Beach Spring Rally for a week, with several visits to the Delmarva Rally and Wildwood, NJ's Roar to the Shore. In 2010 I retired and gave myself a gift of 11 days at the Sturgis Rally and returned a second time in 2013 to see whatever we missed in 2010. All of that was great times with great friends.
In 2012 my Brother in Law bought his first RGC. I rode it and couldn't believe the power difference between that TC 103 and my 88. It took a while for the shark nose to grow on me but it eventually got to me. So, when the 2015 Rushmore RGS came out I made the leap. The RK was getting some serious miles on it but I wanted to keep it. It broke my Heart to trade it in but couldn't afford 2 bikes.
An amazing flashback occurred while I was in Sturgis. We stayed in Spearfish and there is a drug store in the center of town. There was the identical Honda CB 160 Black and Silver sitting on display in that drug store. Could not believe my eyes.