After owning 2 and customizing the last one with $10K+ to my liking my insight is it's a pride thing. Not necessarily reality or market value. Both Fat Boys were excellent bikes. Never a problem with either. The last was a 2003 Anniversary that I did up. The insurance company took possession of it with 45,000 miles after ~ 9 - 10 years. Totalled. I had +/- $30K in it. They started at $8900. I was insulted!! I ended up with ~ $12,500 on a base price of ~ $18,000 after going back and forth several times and providing a list of every thing I had done to it, the Harley part number and cost. Finally told them if it kept up I was going to charge them for the labor I put into it too.
Be patient, there are many in garages owned by old guys for that one time Harley experience with low miles that are pristine. Stroke their ego, make an offer and walk without getting caught up in the 'glamour' that the owner has. Leave your phone number. You should be able to eventually find a nice one for under $10,000. The market has softened quite a bit so it should be more of a buyers market. Couple more cold months can make a difference.