Hm... so instead of picking out single episodes, and watching and reading in a certain order, it's a matter of meshing all of Trek TV with all of the Vanguard series. It's a more holistic approach than the piecemeal-ish list I was looking for. Which is even more awesome, when I think about it, but it leaves no shortcuts for me other than to watch all of TOS... which really *is* something I should get around to doing anyway...
The original series is probably the best Trek, which is one of the things that attracted me to Vanguard in the first place. However there are some differences in tone and the type of storytelling done in Vanguard compared to TOS. Most of that comes from the fact that society isn't as uptight about certain things any more, I mean TOS was shocking by having one of the first bi-racial kisses, I can only imagine what people would have said if they could have read Vanguard back then. But once you allow for that difference, the two mesh together really well.