It seems to me that the problem with Ray’s will is that it forced his wife to remarry. The will imposes two conditions.
One That she remarry.
Two That the person she marries is not named Raymond.
It seems that she couldn’t get anything until she remarried someone and that someone can not be named Raymond. Realisticly how could you give her the money? When would you know that she had fullfilled the conditions? Couldn’t she marry several more times after Ray’s death? What about her fifth husband could he be named Raymond? When would you know that she would never marry someone named Raymond?
Generally, yep. That’s a “no-contest clause” and it’s permitted in most jurisdictions unless there is probable cause for the contest (probable cause would be evidence of fraud, forgery, undue influence, stuff like that). Some jurisdictions are undecided on the issue (i.e., Texas).
A note on estate planning: if you’re going to include a no-contest clause, have the sense to include some kind of gift to the people you plan to disinherit. Otherwise, they have nothing to lose by contesting the will, so they might as well contest it.
I ain’t a lawyer, this ain’t legal advice, blah blah blah.