So people used the same argument with games and loot boxes. But even if videogames cost $500 a copy, there is so much money to be made with loot boxes that they would still exist in these games at that price.

I don't think this is true, but if it is, please provide a link to prove the assertion.

I doubt that companies are selling software at a loss with the intent to make it up in ad revenue. They're selling the software at a profit, and then getting ad revenue for additional profit.

All this just to "maximize revenue potential" for a bunch of faceless investment funds.

Let's be honest though, if a company can make money doing something they most likely will do it. It wouldn't matter if you paid $100,000 a month to use windows, if they could make an extra $1000 selling your personal information and pushing ads at you they will.

The value of marketing to Windows users is in the network effect. If one Windows user can pay $1000 to avoid advertising and change nothing else, the other users will probably hear about this and take notice. But if every Windows user is subjected to ads, I very much doubt that Microsoft is making $1000 in advertising revenue from just one person.

Microsoft would never convert 100% of users to "ad-free" paid subscriptions, at any price. But they can make money directly from advertising to 100% of their users, and there is no "loss" except from attrition (which I would guess is still probably quite a bit smaller than their numbers for overall user-base growth.)