I just wanted to throw this out to you guys since I have really respected your input with purchasing my new bike so here we go.
I purchased a 2014 ultra classic a few months ago but didn't trade in my 2006 Boss Hoss primarily because my friend and I were purchasing two bikes and I didn't want to mess up the deal by throwing a trade into the mix. I also was still questionable if I wanted to trade it in. Well yesterday, I went by and looked at a 4 door jeep wrangler for my wife and just for the hell of it, I threw the boss hoss at them along with her current jeep, thinking they weren't even going to entertain the bike and they actually came back with a pretty fair offer.
Now the question is, do you think I would miss the Boss Hoss when I have a 2014 ultra classic to ride? I purchased the new harley so I could do more long distance rides, ride it more often to work since it has storage, and so my wife would be more comfortable. The boss hoss has been a fun and reliable bike and I love answering everybody's questions every time I park it somewhere but I'm thinking about maybe parting with her. I was actually hoping the jeep dealer would have come back with a crappy offer so I didn't have to make this decision. With that said, any input is appreciated.

 

If you have room to store your Boss Hoss, and if you can afford it financially, I say you should onto it, unless you think it may continue to depreciate.
I've held onto bikes before only to lose money on them due to depreciation but I just wasn't ready to let go of them.

 

I still like the Boss Hoss, it's just hard to justify two bikes with the short riding season we have in New England. I have a garage to store it in but it's not heated. This spring when I took the Boss hoss out, I had a hell of a time cleaning up some of the chrome after sitting all winter.

 

Living in Old England, Boss Hoss's are as rare as rare things, but by coincidence we went to a local bike event on Sunday and there was one there, complete with 502" plus nitrous. Created quite a stir! How could you get rid of it?!

Tiggywinkles in my avatar is a local wild animal hospital, which started by saving hedgehogs and is named after a character in a Beatrix Potter children's book!

 

Like you said, you've been considering selling the Boss Hoss. Enough so to almost put up as a trade in once, and then did so when the second opportunity came up. You've got an offer you like on a bike you're interested in parting ways with.

 

I forgot to mention that I put the Boss hoss on craigslist for $23,000 a month ago figuring I would get a offer around $20-21k but instead didn't even get one call.

 

If you are the man in the picture then keep it. That alone will get a conversation going.

 

It's a very unique bike, and a lot of money. To the right person it's a wonderful opportunity, but those right persons are far and few between.

 

I'd keep them two. Place 4' x 8' plywood underneath your bikes and cover them with king sized sheets then you're good to go during the winters. Moisture and Condensation is your worst enemy so keep them covered in order to stay dry.

Thorey

 

i have a second bike, not a harley but a yamiha Road Star Silverado. Is a 2006 i got in 2005. i rode the pi$$ out of it back and fourth to work. i got it because i was entering back into the bike world and wasn't sure if i would ride enough to justify a Harley. I bought a new Electra Glide Ultra Classic in 2010, after putting over 30000 miles on my Yami and quickly put 14999 before trading it for my 2013 FLHTK which is now about ready to turn 20000 miles. I'm at the point where i'm about to get rid of it. i was keeping it for my nephew but kids and dogs came along in his family and his priorities changed. So, i get where you are coming from. i of course don't have the unique item that you do but it was my first entry back in the riding arena. Someone should get the pleasure of riding. i think i would throw it at the dealer, especially since you haven't even had a nibble on craigs list. Good Luck!