Classic iPod isn't recognized in iTunes / Cannot Sync

My iTunes is up-to-date with 12.1.1 version.

I have a Classic iPod that was working fine until the last 2 updates.

Now it's not recognized and, therefore, won't sync.

Here is what happens:

(1) Open iTunes. It freezes

(2) Finally opens. Plug in Classic iPod. Sometimes icon shows sometimes not. Have to often manually eject (Windows 7 won't let me as 'it's in use').

(3) Once finally showing. Try to Sync.

(4) Get error message stating computer isn't authorized. (Have already deauthorized and reauthorized several times).

(5) Then get message with 2 other UserIds that they need to be authorized or I will lose 40 songs. (Have authorized those as well).

(6) Then get error message that device isn't recognized. I have run diagnostics in iTunes as well, Device isn't recognized.

I am fairly computer savvy, but not a computer expert by any means. I hope that this is an easy fix. I am concerned my iPod has outlived its time with all of these new updates. Also, wondering if there is a driver or something I need for my iPod.

Would appreciate any help I can get. Thank you!