For me it wasn't so much about price and resale, I usually ride 10k - 15k miles a year at least and keep my bikes a long time. By then resale isn't in my consideration. However I know what you mean, if I changed bikes every couple of years I'd never buy a new victory since they depreciate so much vs harley. Nothing against any other brand or style of bikes, 2 wheels is always better than 4.
For me it's never been a question, I'm a Harley man and always will be. I'm proud to support an American made company that's been pumping out bikes since 1903.