How does one count users? I previously used a Skype account, but now I share a Skype phone with my girlfriend and her account. I'd guess there are plenty of families with one Skype account.
with skype all they do is look at unique logins per financial quarter, so in your scenario (and I assume it is common, because I have my own family members doing the same thing) it will count as a single user
perhaps they should adjust their terminology and refer to them as 'accounts' rather than 'users'