Even if he hadn't toured, it would not really displace his concerns since I think they are probably more relevant where he at the window looking in than not. I think a lot of people do worry about where they will sleep, and I have toured in areas where the primary modes are illegal. It is certainly difficult to be aware of all the ordinances for all the jurisdictions one travels through. This is one of the reasons for stealth camping, don't draw attention when one will end up on the loosing side of any argument, even if one is in the right.

Around here bike touring is vastly unpopular, and there is no way there will be accommodations made to make it easier. Stuff that is hugely popular like fishing, has been waiting decades to have minor sensible adjustments to the regs made. I think the main option will be backdoor solutions over the internet. Changing the Taxi licensing system would be tough. Comparatively Uber is simple.

An example of something not entirely unlike what Tandem is after is the Walmart system for allowing campers to use their lots. Sorta odd really, one would not expect Walmart to do something oddball like that. Around here there aren't any 24 hour stores, so it is more than possible to set up in Walmart after driving till dark and spend not a dime in the stores. I am not aware of all the issues this may have caused, it seemed superficially to be a mater of saying come on in. They aren't charging for the service, so that may work. The question for small camp ground folk would be how to get paid, if that was an issue. But there is probably a way. Like maybe a purchase over ebay, that will be difficult to track the reality of. Local pick-up only.