Boy, you just seem to have all the bad luck in the world with Amtrak!I've lost hundreds of dollars over the years on tickets that didn't print or were damaged or simply went missing.
Having a credit card charge didn't seem to mean much if anything to Amtrak counter staff.
Amtrak OBS staff were almost universally positive something could be done to recover the value.
Unfortunately the ticket counter staff were equally positive nothing could be done but buy another ticket.
I travel Amtrak far more than you do and I've yet to lose a dime on Amtrak tickets because of a machine malfunction. And in fact, I've only ever had 1 Quik-Trak fail to print my tickets after I started the process of obtaining said tickets.
I've seen a few machines that were clearly out of commission of course, to the point where you couldn't even start to interact with the machine. But again, only 1 that started to work with me and yet failed to accomplish the job.