This seems to be missing the point of Kolmogorov complexity. In Kolmogorov complexity we aren't concerned with the complexity of some fixed finite string, for this very reason.
It's the latter. I use LastPass too, and there's one particular site where it doesn't autofill, because of autocomplete=off. It's just one site, but incredibly annoying because I use it often multiple times per day (and of course it doesn't allow me to stay logged in either.)
Maybe, but the author mentioned that he wanted to reverse engineer it as a black box, out of legal concerns. It makes a more interesting challenge this way too.
I too tether without paying (Nexus 4, to my laptop). I don't usually do it too heavily and until recently hadn't had any trouble from T-Mobile.
When I moved into my new apartment I used it more than usual (maybe 2-3 GB over a few days) and they started redirecting my traffic to a "Pay for Tethering" site. It's just user-agent based though so very easy to circumvent. Other than than I have had no issues.