If only I could use my pw manager at the windows login prompt.

Exactly. My university requires a yearly password update. I have to manually enter my password to log into computers, print release stations, a billion domains that just use an LDAP connector instead of our Shibboleth page, servers after home directory wipes, etc.

My password needs to be something I can quickly type, so I just use the same one (a strong, multiple-word passphrase) and add its validity period to the end.

This actually makes hitting arbitrary password requirements easy too; make one word capitalized (or one lowercased), separate each with an allowed symbol, and the validity period is numeric so it passes just about every security check while being easy to type and remember.

Indeed, my work login password, with regular rotation requirements, has been dropping entropy by a few bits each time it comes up for renewal. I work to make my work passwords as different as I can, but that password doesn't get used enough for me to trivially remember it, and it can't be offloaded to a password manager easily.

I store a 32 char random string on a yubikey and have it setup so a “long press” on it enters it, works pretty well...

I'm curious why you use this and not the Windows integration with yubikey?

https://www.yubico.com/products/computer-login-tools/

I'm on a Mac and couldn't be arsed setting it up properly ;) It's fairly easy to put a static OTP on two keys incase I lose one also instead of trying to register two with the OS.

Also I can use it for various other things (like password manager secret etc) which don't support yubis out of the box.

1password syncs to your phone. I can count on one hand the number of passwords I actually have memorized

I use 1password for everything, but I need to type my professional Windows password every time I log in, I'm not copying a password from my phone every time I come back from the bathroom.

They've allowed third party fingerprint scanners to handle login so the APIs are there to do it.

Indeed. I use a passphrase, or a series of typeable but random words in the 'correcthorsebatterystaple' vein for that.

I used my PW generated password on a site earlier, the site refused to accept it. 2^102 bit aren't enough (18 from 52 random upper/lower characters) aren't accepted, but P@55word was fine.

Password must between 6-12 characters...

rips hair out

This is _specifically_ the one place where we require a rotating password too, so I think those experiments are informative.