Just playing the "Devils Advocate" here:

Years ago, back in the days when H-D's didn't depreciate very much (if at all) it made sense to frequently sell the old and buy the new.

On all of my H-D's (from '75 to '97) I lost very little money on them, not counting parts and service.

Today, the resale on used bikes is "in the toilet" and you practically have to give a used bike away and then spend a small fortune to get a new bike, but the longer you wait and the older your current bike gets, it takes even more money to buy a new bike!

Used bikes (if they were well taken care of and looked nice) used to reach a "price floor", but these days, the folks who have a lot of money are willing to take a huge loss on their bike in order to get a new one with all the new "bells and whistles" and that's driving the price of used bikes (regardless of condition) into the ground.

 

not far behind ya. I owe $3500

 

Splurge on customizing it, and bank the rest...

It's easy spending other people's money.