Bought my first Harley in 1991 and sold it in 2001 for more than I paid for it. Ah - those were the days!

 

In May of '09 I bought a new SG and in October of the same year (6 months) sold it for what I paid minus taxes.

 

You could work out the answer based on historical prices here.

 

A long time to OP question.
My 94 has an outstanding offer from a fellow rider for $10K as we speak and I'm still debating about it.
I sold my '89 Springer in '96 for $14K (paid $13K otd new).
I sold my Low Rider for $5K, paid $5300 in Reno for it new with bags, diff seat & pipes.
my 2 cent history!

 

Miles, Miles Miles, If you put miles on it you'll pay for it. I have a '06 Ultra and dealer will give me 10.5k for mine with 43,000 miles. They have a '06 with 9,000 miles that they want 15.5K for.