None of your mailers meet the conditions of your users subscriptions. Some also can't logically happen. I've reviewed them all and my comments regarding their configuration as follows.
Post Expiry Email
This mailer is configured to send 2 weeks after the expiration date, but it's checking that the status of the subscription is Active. After the expiration date means it's Expired. So this mailer is in an impossible state. You need to change "Must be in state" to "Expired", but honestly it can be set to "Not relevant" as you're already conditioning on the expiration date so the status doesn't matter (it'll be expired).
2 Weeks before Expiry
This one appears to be configured correctly, but I see no subscriptions that match its requirement. It's only going to send 2 weeks before a user expires and only up to 3 days later. So 2 weeks + 3 days is the window that it'll send. Once out of that window it will no longer attempt to send.
Expiry Email
This one is configured to 12 hours after the expiration date, but it's checking that the status of the subscription is Active. This is the same problem that "Post Expiry Email" has. You need to adjust "Must be in state".
1 Month Before Expiry
This one also appears to be configured correctly, but I don't see any subscriptions that match its requirements.