Ooh, what if barb wrote her will to say Cole gets the house and all its contents, but in exchange he has to let Chris live with him? That'd be totes drams.
You were basically inviting legal sperging with this, but whether such a will provision would actually be enforceable would depend on how it was worded. This is essentially a defeasible estate. The question would be whether it would be a fee simple with an executory limitation or a fee simple subject to a condition subsequent.
Such a will would have to be worded pretty carefully and with respect to Virginia law, which apparently has quirks about the distinctions between these kinds of estates.
Let's say it was worded as "Snorlax hereby bequeaths Sonichuacre to Cole Smithey, so long as the property is used to house Christine Weston Chandler and the Sonichu Museum." Then, it would basically require the subsequent owner to house Chris and his collection of whatever.
However, usually such an executory limitation would require something else. That is, a third party who would get the property if the World's Smartest Film Critic (if you Google that phrase you actually get Cole Smithey) refuses to house Chris or chucks out his Legos.
Such as leaving it in that event to Michael Snyder.
Other possibilities would be that the property would revert to Barb's estate, or that some potential unspecified third party in the inheritance chain somewhere could jump up, recognize the violation, and demand the right to claim the property.
This is the kind of question that fills the bar examination. The real lesson, though, and you don't need to take the bar to know this, is don't do dumb shit like this in your will! It makes greedy lawyers very happy.
I'll invite an opinion from
@Saul Goodman but he might think this subject is best avoided unless he's being paid to talk utter nonsense about it. Because most discussion of defeasible fees is utter nonsense (until it involves millions of dollars of property then it's really expensive utter nonsense).
Also, for some dumb reason I looked it up. Virginia actually has a
specific statute on this.
I could come up with a good argument that statute means whatever the fuck I think it does.