If we accept that nothing is free, then we have to ask what the best way to pay for the so-called free product. In my mind it's either some sort of usage data, or it's via taxes.
I would guess in almost every case, the purpose of free wifi is not to do any sort of tracking, it's just to get you in the door. I know that I've picked hotels and other establishments based on the availability of free wifi.
Yes, though this is now becoming an expectation. I haven't done much business travel in the past few years, but now that it's ramping up again I notice how important the free wifi is.
I doubt it will be long before this randomization is of no real protection against systems employed by the likes of the NSA and similar. If they can figure it out then a private company could as well and market the managing of free wi-fi services to localities and such all under the guise of better understanding your customers, or worse protection from bad people.