Oh they sure can win.
They can win by not removing the $15 option (which, for our company at least, ended last December).
They can win by allowing people to keep the same benefit which they previously had, which was to allow them to purchase a particular edition (eg, Office 2019) and providing the security updates until that product goes EOL ... like they have in the past.
This is just Microsoft being plain greedy and trying to squeeze their customers even more.
I'm a techie in our desktop support area and you wouldn't believe the amount of people who've gone to Libre Office because they won't or can't pay $70 a year for something that used to cost them, on average, $15 every 2 years.
Given the amount of money that Micro$oft makes from their corporate customers - somewhere around $500 a year per seat for a fairly standard desktop licensing pack (not including server licensing or CALs) - it's a pretty cheeky ask.
The whole marketing spiel of the HUP (Home Use Program) was - originally - that it was to let people effectively "piggyback" off their employers' licence; the thinking being that the employers licence wasn't being used while the employee was using their personal computer at home.
In fact I remember when the HUP was a free perk - that was not so long ago.
But now it pretty much becomes just another marketing campaign.
Like so many others before them, Microsoft are trying to slay the golden goose to get all the money at once. This might not hurt them as much as these practices hurt, say, Nokia, but it's certainly not going to help their overall image in the wider universe.