Selling your Leica to pay off debt will be a waste if you let the debt come back. But if it's part of a plan to get out of debt permanently then, sure, sell it; 'conversation starter' is not a particularly efficient use of your resources.
The only way I know to permanently get out of debt is to stop living. I am not ready to go to that extreme.
Warning!! Handling a Hasselblad can be harmful to your financial well being!
Nothing beats a great piece of glass!
I leave the digital work for the urologists and proctologists.