Started riding at age 50, 14 years ago. We needed another vehicle as my girls needed to drive to high school. Turned over my white van (affectionately known as "Moby") to them and went cycle shopping. Bike history, after I took the MSF course:
1991 Honda Nighthawk 750: Nine months and 9,000 miles. Ran great but was showing its age at 27k miles. Needed chain and sprockets, head gasket, tires, and battery. Sold at a slight loss to a mechanic at the Motorcycle Institute in Phoenix.
1989 Honda Goldwing: Two months and 3,000 miles. Great for distance but wrong for the commuting i had to do. Sold at a respectable profit to a member of the local Goldwing club. Saw it years later when I took the Wing precision riding class, looked good.
1995 Honda VT1100 Shadow: Eight years and 77,000 miles. Commuter and a long trip bike until I retired. Ate fork seals and batteries, handled well, did everything I ever asked of it and never let me down. Disliked the small tank, 3.4 gallon, liked the mileage, 48 in town, and loved the looks. Sold for most of what I paid for it to a friend, who promptly dropped it.
2005 Honda VTX1300S: Two years, two days, and 27,500 miles. Purchased after I retired and for my 60th birthday gift to myself. Great road bike, cheaply made, no personality. Sacrificed to the highway gods in what should have been a minor incident, and settled favorably with Progressive. Had no emotional ties to it and would have sold it soon anyway.
2007 Harley SuperGlide: Just under three years and 37,500 miles. No major or serious issues, just minor stuff like loose exhaust flange nuts and a lost swing arm cap. Several upgrades for comfort and utility, not wild about the silver engine paint. Love the overall appearance, and intend to keep until the mileage exeeds the sum of all the prior bikes. Only bike I've added appearance items to, with more on the horizon. Only bike with a name - wife calls her the 'HARlot".
Would only sell if the right '09 or newer Road King or a late model Heritage or Fat Boy came along and called my name. Right now she's set up just as I like for the riding I do.