Also - has anyone had a CCS upgrade to their pre-facelift Model S?
I don't need CCS (I think) but these are gaps in my knowledge I need filling!
Getting the CCS upgrade to your car is completely unrelated to the CCS supercharger issue - CCS superchargers is only an issue for Model 3 (which requires them), Model S requires the old-style supercharger cable regardless of whether the CCS upgrade has been done. Probably there will eventually be a change to Model S so that it takes CCS directly (and becomes equivalent to the Model 3 for charging), but at present CCS on Model S is via an adapter to account for the plug shape and an upgrade within the car to handle the communications.
So, whether or not you need the CCS upgrade to your car is an issue of what sort of non-Tesla public charging you need. I would suggest that for most people wanting to use the Model S as an 'only' or 'primary' car then you probably need access to public rapid charging, though it will depend where in the country you are starting from and what sort of driving you do.
For Model S, the choices are the CHAdeMO adapter (which is a complex device with electronics in it but requires no upgrade to the car) or the CCS adaptor (which is a smaller, mechanical-only adapter but needs an upgrade to the car before you can use it).
Right now we are at a tipping point. In the past, almost anywhere with CCS also had CHAdeMO and the CHAdeMO was typically more reliable, so the CHAdeMO was the better bet and having got one there was no point in getting CCS as well. However, CCS-only locations are starting to spring up (notably ionity) and in the future clearly CCS will be the better bet. Right now, CHAdeMO is probably slightly more useful (on account of the reliability issue), but having both would be ideal.