I think both of these scenarios, at a minimum, will require a high degree of "FSD" before being truly practical/approvable. Yes, it sounds easier to have cars driving around at night on "empty" roads, but unless there is going to be some kind of rule that non-self-driving is outlawed during certain hours, the roads cannot be guaranteed to be "empty". Plus, the scenarios in which driving to a central charging depot would be most beneficial (in denser urban areas where there is a lack of off-street parking) would be the ones more likely to NEVER have truly empty streets at any hour. Plus, if you don't have off-street parking, wouldn't you have to call for the car to come and pick you up (or drop you off) during hours when by definition there are likely to be cars on the road?
Maybe in an apartment complex or parking deck where the vehicles would not have to go off-property, but a better solution for that might be a robotic L2 charging station that moves from car to car, not the other way around.
I don't think this would be a totally reliable method. Better than what we have today, yes, but in this hypothetical scenario, are you thinking that some people would forego the automated queuing/parking system to serve as "pluggers/unpluggers"? And would this require some kind of staging area for cars waiting/completed to park?
Me too, but on the other hand, most of my Supercharger stops are not sit-down meal types. I suppose that the ability to queue & park might open up more use cases where I would take a more casual approach to charging, but just having returned from an 1800 mile road trip (pretty much the only time I use Superchargers), most of my stops were in the 10-15 minute range, with a few under 10 minutes, and a a few as "high" as 20 minutes (suggested). On the one or two stops that I did sit down to eat, it was not that big a deal to get a few extra minutes while plugged in (maybe I charged to 80% instead of the target 60%). And none of the chargers were full anyway.
I suspect that in 5-7 years we will look back at this discussion and decide it was a solution in search of a problem, as I expect there to be pervasive charging options available in many outlets, if only because said outlets will need to keep up with their competition that already offers it (i.e. snowball effect) and the age of constrained charging will be a thing of the past. They might not all be 250-350kW high speed chargers, but a bank of 4 100kW (or even 50kW) chargers at each and every restaurant and convenience store outlet is going to lessen the need and use of mega-charger complexes.
BUT, if there is a need for some kind of semi-automated charging solution (either for road trip or central charging depot use), I could imagine a site designed with a well organized staging area with a confined and well defined path from the drop-off area to the charging stations, and then to the pick-up area. I do think that while navigating streets is complex, navigating a parking lot has its own unique challenges as it not necessarily simpler than driving on streets, at least one shared with human drivers, pedestrians, and other obstacles. But a more or less closed off area could be a far more controlled environment to operate in.