It's fine to have those domain names, but they need to redirect to a specific page of one singular site. For example, TheDonald.win should redirect to [sitename].win/TheDonald, and KotakuInAction.win should redirect to [sitename].win/KotakuInAction.
This is the only way for it to really work, and this is how we will grow. As things are right now, it will become impossible to differentiate between affiliated and non-affiliated sites with .win domain names.
Maybe .win domain names should be registered as random numbers and a database should be used for direction to different subs. That way people can’t go out and register .win domain names and sit on them. Users would need go through a master landing page to connect to a desired sub.