"Any thoughts?"

You posted in the Community for peer users of ProSeries income tax preparation program. I'm not seeing a tax program or preparation or filing question.

Tuition remission is not taxable if it meets the nondiscriminatory rules. You can give differing benefits to Admin vs Teaching staff.

You didn't state which type of entity they want to operate under, if they got their approval from the local school district per MA requirements, etc. You also didn't mention if this is an Independent private school or an Affiliated private school.

Everything matters; and more details for what help exactly you are looking for, would be helpful, too.