That is an incredible list and I can imagine its merit. (It also humbles me as I realize how much there is for me to see!) However, as someone who is now a little more than halfway through TOS having never seen it or a single episode of DS9, VOY, or ENT, I think that probably is better suited for someone who knows more about Star Trek than I do. As R. Star
stated earlier: “While Enterprise takes place before TOS, it contains numerous references and easter eggs to what comes after it in the timeline that to get the full experience you really should watch it after.” Since I would be almost certainly oblivious to much of those, I think my first experience of Enterprise should probably come after so much that came before in production. More familiar with the series, or perhaps a second watch-through, I think a fully chronological time-line order would be fantastic.
That will be great, once you start watching by airdate. You'll be moving from Voyager to Enterprise back into TOS (to start over), which means you'll be watching both by airdate AND internal chronology.
That's my own plan.