[Jeff Higgins]

There are way too many nuances to cover them all, at least until one narrows the range a bit. Of the bikes you show, the '08 Sportster is the one most interesting to me. The '12 Dyna (if legit) is a fantastic machine, but a horrible motorcycle. Reliable as a stone axe, but riding it will feel like being beaten by one.

In general terms, newer is, of course, better. Big twins from the Twin Cam era, Sportsters from the rubber mount era and newer. These will be absolutely dead reliable and require virtually no maintenance outside of fluid changes, brakes, and tires. Evo bikes are still pretty good, especially the rubber mounted ones, but the hard mounted Sporties still vibrate like paint shakers.

Shovels, Ironheads, and older are definitely "hobby" bikes. While I never rode mine cross country like afterburn, I did ride my '76 Sporty to Sturgis and back home to Seattle with no trouble in the early '80's. I was a younger man then - I still have that bike, and an afternoon on it today has me laying on an icepack when I get home... Plus I do tinker on it fairly constantly, just to ensure it is ready to ride when I want to.

Yes, today's market is flooded with fantastic used Harleys. Truly no-issue, ready to ride, and cheap. Production went through the ceiling in the 2000's, and minor changes keep coming. Guys who absolutely need the "latest and greatest" dump low-mile, fantastic bikes for a song. It's a buyers' market out there.