We've officially started our journey by getting split up right off the get go. Minxter got on a different plane than I did. That's the way it goes when you fly as a 'non-revenue' stand by passenger (buddy passes). You are at the mercy of fully booked planes and you just wait for the next plane that's not full. This can be days if you're unlucky and dealing with any checked bags is an additional challenge. You also are responsible for getting all the flights lined up to your final destination which includes buying any shorter flights where the non-rev option is not part of the program. The whole thing can be very trying. You just need to let it go and be ready to improvise.
However, you can have a totally different experience when there's room and you get offered first class seats. This however cuts into the minimalist approach as you need to dress appropriately and respectful which means you can't wear your dirt bike gear on the plane like any self respecting minimalist would.*
So, we're in Detroit waiting to see if we get offered first class.