As someone who used to work for a H-D dealership, all the “extras” you have put on it (assuming you have) like chrome parts and other accessories, expect to get nothing for those. We always suggested to customers to take those off and sell the bike as close to stock as you can. All those add-ons are to make the bike the way you want it. Then, when selling, it puts you in a box to find that person that has your taste.
I keep all my take off parts to put back on when and if I decide to sell a bike. Craigslist is good, as you can tell the real sellers from the fakes pretty easily. Facebook marketplace and eBay as well.
Don’t take life too seriously. You will never get out of it alive.