Identity Safe Website Password Changes

Long ago, I tried Identity Safe and found that it wouldn't accept changes I made to passwords after I first stored the old one in the Vault. That is, it wouldn't recognize the new password and replace it in the Vault when I reset it. I am ready to try again with the newest version.  Many of my old passwords are dreadful.  I am working on changing them to strong passwords. 

ANY ADVICE on how to fix about 100 passwords with less pain??

My question is:

Should I update all my passwords to strong ones before I open my Identity Safe Vault and get it going?  

Will the current version support password changes easily? 

I also have printed the instructions for 2 page logins as I need to do that too.