When I started using a password manager I did something similar, but I told myself every site which used the "insecure" password was linked. So I'd ask myself "If someone hacked the least consequential site I've used this password on, they'd also have hacked this site, do I care?"
It was very rare that the extra 30 seconds to add a new entry password manager wasn't justified after asking myself that question.
I think it all comes down to ease. Yes, some secure passwords is better than none, but it's just soooo easy I'd just say go with the PM