In this case, the benefit sought is not so much about time and money, is it? It's about demonstrating acceptance, setting an example to the broader society?
Anyway, it does sound like a player is going to break the rule. Laughton, Merrill, Huberdeau have commented about it already, I don't think the NHL was thinking very clearly about this, and they're going to pay a price in negative PR that they somehow failed to see coming. There will also now be players wearing hats and t-shirts and whatnot in interviews and off-ice events, and it won't fail to be noted how that relates to the NHL's silly tape rule.