Not just small free apps. Oracle would install the Ask toolbar when you installed their database server, unless you noticed and un-ticked that option in one of the installer dialogs. Oracle.

IIRC for a while the official Java runtime installer also installed the Ask toolbar.

It's worse now because browser extensions auto-update which means that when a malicious actor buys an extension they gain access not only to future users but to all current users as well. Also, the Chrome Extension Store publicizes how many users each extension has, which allows malicious actors to operate extremely efficiently as they can easily find extensions to acquire and they know exactly what they're buying.

And even worse, because they don’t only hurt performance and usability, but they also report private information. Even is the data is sent anymously, the url itself may contain private information. For instance, Google themselves still allow sharing documents via a “private” link which is then stored on some monitoring service. And some of those services allow anyone access and search these urls for some premium plan.

"our parents and grandparents, basically."

I now feel officially elderly, Cheers for that. Lol.

I think the implication here was that your parents and grandparents were less computer savvy at the time. This resulted in them installing all kinds of toolbars that destroyed performance.