One major difference is the incentives indirection. Google's revenue comes from ads, not end-user software, whereas the Microsoft of the '90s was much more dire

One major difference is the incentives indirection. Google's revenue comes from ads, not end-user software, whereas the Microsoft of the '90s was much more directly connected to their users. So I'm not sure which is worse for the user, but it seems like it could make Google's situation worse because the signals they get from their "users" aren't necessarily the highest priority. Up to a certain threshold, enragement is engagement which is a positive short term signal for an ads company, with potentially bad long term consequences.