I can't remember the last time I've needed to answer security questions for that unless I was trying to recover an account without an email, except maybe with online banking.
Someone might be 'recovering' your account right now...
Also, you're proposing everyone use a separate password for every site, so now they have to keep track of all those passwords somehow. If they put them in some password manager, they're back to the issue of trusting all their credentials in one place. And now that's increasing the chance of non-tech-savvy users doing something like keeping them in an unencrypted text file.
It's just not an issue with a password manager, in fact it keeps things more secure and is so much easier. That said, yes, you have to pick a good one like PasswordWallet by Selznick or maybe 1Password (non-cloud version).
I get what you're saying about non-tech-savvy... but if they don't get tech-savvy enough to use a password manager and some basic common sense, they probably shouldn't be using tech in the first place. If you think they are in trouble now... wait a few years.