I think it's funny when folks say Harleys hold their value. If you pay 27000 for a bike and sell it 5 years later for 21,000, did it hold its value more than paying 13000 for a sport bike and selling it for 7000. On a percentage yes but in real world dollars in my wallet no!
We have a hard over Harley rider in our office (It's the only bike and all others suck) and I can say I have over 19000 miles on my bike in 2 years and he has less than 10000 on his. So far he has had his shifter pedal fall off, had to deactivate the automatic shut down of the rear cylinder due to pinging (they couldn't fix it), had it remapped twice for altitude and had to replace a sensor on the primary because it was leaking oil. So far on my bike its been oil and tires and air filter without a hiccup. Besides, I can go really, really fast!
I was seriously considering a brand new Ultra Classic for two up riding with the wife and am now considering a BMW or Used Gold wing due to the problems he's had. Although one might consider them minor, I think if you spend that much, it should run perfectly.