> Despite this, I'm realizing I want to make the move before these old systems break down, especially so I can make sure the old files are transferred over and

> Despite this, I'm realizing I want to make the move before these old systems break down, especially so I can make sure the old files are transferred over and old passwords synced to new devices. Sounds like you need a data backup policy more than a hardware EOL policy. If your data is secure, run it until it dies, or you need more than it can do.