Based on the TV guidelines, it should be its own entry.

I disagree and support the addition of "Joe Bob Ruins Christmas" and similar specials, since everywhere they are listed as "specials" of "The Last Drive-in with Joe Bob Briggs". To create it's own entry for each new special is cumbersome and will make everything more confusing over time.

They are listed on the Shudder website as separate series, not as specials. Consequently, they should be listed here as separate series.

The fact that other sites list them differently has nothing to do with the way they should be listed here. Each site has its own set of rules.