Help hardening my login passwords

Thanks for the guidance, @ag_yaron. Life (and a hurricane) interrupted my project, but I'll be back on it in a couple days.

I'm thinking I'll start out hardening some silly sites (Dunkin Donuts, Waffle House, and the like) before I take on the more important ones (Schwab, Fidelity, and Citibank for example).

Do you have a feel for how often 1Password's Smart Password functionality actually works to conform password creation to site constraints? Never, seldom, sometimes, often, always? I'd like my "hardened" passwords to be as robust as possible, but I don't want to waste time and energy if the feature has little application in the real world (as it exists now). Thanks again.