Chase will put a note on your statement 2 months ahead of the AF charge stating the date it'll be charged. Even if you have a $0 balance, they'll cut a statement to send you that note so just check the statements each month. In practice they charge the AF the first of the month following your anniversary date. My CSR/CSP anniversaries are this month so I'll get the fees on May 1 (and I got the notice last month about it).
If you downgrade the CSR to a CSP you will get the lower $95 fee. The first AF is only waived for new card applications, it was part of the sign up offer. You can also downgrade to a CF or CFU instead for no fee if you already have a CSP.
Unless they cause you anxiety, I wouldn't close the no fee Disney or
Amazon cards. They aren't really hurting anything keeping them. If you don't use them you can reduce the CL on them to free up available credit for new cards. Just put a charge on each once a year to keep them active and let them help anchor your age of accounts. The Disney Premier card you could cancel if you won't be continuing to use it to the fullest. You can always PC one of your no AF cards back to it if needed and even sometimes Chase sends out offers to do that with a statement credit to offset the AF. EDIT: Forgot to say, if you stay under 5/24 you could always reapply for the bonus after 24 months too.
As for the keeping the CSR or CSP, there's a few strategies for that. Like the Disney Visa, if you have a 10k CL on a CF/CFU/CSP you can PC back to a CSR when needed (likewise to a CSP if you have a 5k CL). So unless you need to transfer UR's to DH's FF/Hotel account, you could probably downgrade his CSP while you hold the CSR and then evaluate what you'd like to keep going forward when your CSR comes due.