I just got married, and my wife and I are in the midst of combining finances, etc.
We set up a joint bank account and the first thing I do during the account setup phase is generate a 16-character password with LastPass.
No, don't do that! How can I access it if you use LastPass? Just make it something simple to remember!
We compromised on that one - I generated a password that we both agreed on that's reasonably long with a mix of characters, and yet it's something that she can remember off the top of her head. (Never mind that with LastPass you can share passwords to various accounts, without either person actually even knowing the password!)
My wife definitely fits into the "average user" category as opposed to the "power user" category. I've been able to convince her to turn on two-factor auth whenever possible, but for the most part she is unwilling to trade convenience for security.
Obviously, it doesn't need to be this way. I use LastPass religiously, and she sees me use it regularly to generate and use passwords. I'm in her ear fairly regularly about the importance of password security (see various institutions getting hacked - which I don't really believe were anything sophisticated, just poor IT infrastructure because of management thinking IT is not "value-added"), etc. She (and a lot of my other friends) are quite content with having the standard 4 passwords for all their websites. They don't really see what the point is of having more difficult passwords. For my wife, it's "I'll set up LastPass some other time, it's not really that important anyway." I think everyone on this SE would think that it truly is that important.
I really don't understand what the hang-up is with using a password manager, but then again it's so obvious to me why nobody should leave home without one. How can we computer-savvy folks educate/convince/etc the non-computer-savvy ones we care about to take their own security seriously?