As far as pre-paid exenses go, that depends on the contracts signed (if any), who are the parties to the contracts, and which jurisdiction's laws apply to them. Not knowing those things, even a legal professional can't say if it's legal.
But whether or not it is legal, unless somebody pushes back the result is the same. An exemplary (sheep-like) Witness is unlikely to question decisions of the Watchtower Society, so most often the Society will have their way. Tech49's example illustrates how this works: the brother surrendered without significant resistance, and the Watchtower Society wins by default.