There are definitely good deals out there to be had. My neighbor has a 2007 Road King Classic with 1900 miles that she is selling. Her husband passed away in 07 and she hasn't let go of the bike, even though I have obtained several reasonable offers on it for her. The fact is, she's not going to get more out of it than someone selling one with a lot more miles. At this point, I doubt that she'll get more than $12K to $13K out of it, and very unlikely to top $14K. Really not bad for what is essentially a brand new Harley. There's plenty of Harley's sitting around with virtually no mileage in peoples' garages that they are ready to part with. Start asking people you know to keep an ear out for anyone looking to sell. You may be surprised at what you might find.
The price of a Harley is only high if you buy another brand. Why, you ask. I bought a 2006 Yamaha VStar, even though I wanted a Harley. After adding $7k to $8k to it trying to make it look and sound like a Harley, I finally broke down and bought an 07 Road King Classic, once I realized that no matter how much I put into it, it still wasn't a Harley. I lost a bundle when I traded and if I would have just gone for the Harley, I would have saved many thousands of dollars.
I have never looked back. My Yamaha was a beautiful bike and it ran great, but I was never really going to be happy with it. Every time I pulled up next to a Harley at a light, I remembered what I really wanted. For some mystical reason, there's a lot more to owning a Harley than just the bike itself. It's a huge family, with open invitations galore to become a part of it.
I think that what I am really saying though is that once you have the itch, it won't really go away until you scratch it.