[Grizzled Bear]

Sounds like a good price for the Harley and it will certainly hold its resale value way better than the Yamaha. The Yamaha is quieter, smoother, and better for long distance travel, but may only be worth about half of what you paid for it in a few years.

The Yamaha dealer already knocked about a quarter of the price off of what is virtually a brand new bike, even though it's an 09.

Another concern is the cost of insurance. Do Harley's have a higher theft rate than Yamahas? I'm checking with my agent next week.

[Eye of Unk]

I have heard that the Harley will be stolen no matter how much you try to prevent it while a Yamaha will likely be ignored. If it was such that you think it may be damaged easily, trashed or stolen then why spend $20,000 on a bike?

Its sounds like you are pretty much decided on the 2009 Yamaha, if its the same model as mine you will want to change the bars out for some more pullback. Yamaha made the position too low and too far forward for most people, the 2010 model corrected this with a different bar and seat arrangement. And I hear the “Ultimate” brand seats are the best.

[Errant]

On the insurance, it is very minor difference if any. Check the price of a similar used 5 yo Yamaha on Ebay or Craig's List and you'll see what a beating they can take on resale. Figure that into your operating/ownership costs.

Owning a Harley is one of those bucket-list items for many people and there is the kool factor that can't be ignored. That said, I couldn't imagine being without a motorcycle of some kind! I've been riding for 40 years. My first bike was an Allstate scooter that I bought for $15 and carried home in several buckets.