He is basically asking almost original MSRP for the bike ($26,999 MSRP), so I'm guessing he paid way over MSRP and wants the next guy to help him recoup some of the extra money he threw away. Or he has fallen for the old fable about how Harley's retain a very high percentage of their original price (low or no depreciation); if so he is delusional and hasn't been paying attention for the past ten years. Btw, NADA shows average retail at $17,500 for that bike. Bump it a grand or two for low mileage if you want, but it's still worth maybe $20k max.
As VaEagle mentioned, it ultimately comes down to how badly you want the bike. If you really want to pay MSRP for a five year old bike, that's up to you. I think I'd do as previously suggested and just give the seller a best offer price and let him know how long you'll wait for an answer. I always assume people asking way too much will eventually come to their senses when no one bites, but I've been wrong on more than one occasion. They can always find another guy just like them who will pay way too much. There still seems to be a fairly large number of people who continue to think it's still 1999.
JMHO - Jerry