Yeah, it's a little sloppy and I think it misses the mark, but here's kind of how I'm seeing it.
It's for people with money that want VMP to curate their record collection for them. They listen to indie bands and have "eclectic" tastes, but really just hover within the same parameters of what is played on non-commercial radio stations like KEXP. It's kind of like how SUB POP is considered a indie label, but Warner Bros owns 49% of the company. They only go so far off the grid and are still fairly tethered.
Even by looking over that Day Of The Dead box, I could pick more names of artists whose takes I'd be interested in hearing about regarding the Dead. Having some dude from Dirty Projectors or someone from the Decemberists talk about them is not a selling point.
I remember 15 years ago, when the psych rock revival was really starting to gain some traction and talking about how ridiculous it was to me that there was still so much aversion to the Grateful Dead. People were starting to embrace this throwback sound, but continuing to completely dismiss some of the primary architects. It seems like a lot of people can't remember that the Dead were still considered "uncool" and something to run from. But, shortly after, their legacy started to infiltrate that scene and then, almost overnight, they were given props. Even if you didn't listen to them, it was a good idea to wear a shirt. I saw images of some high fashion runway show recently where they all had on tour Tees.
Even now, when some people are explaining that they dismissed the Dead it was because they knew people that also liked Phish. The Dead's stigma was the same as the one with Phish, if not worse Phish actually took on some of it that they still retain, after the Dead has shaken it. That's because, prior to recently, people who listened to the Dead were considered a certain type of person. Once you start to see that the music reaches beyond that small stereotype, it's harder to argue that case.
So, now there is an acknowledgement that they overlooked the Dead for whatever reason, but for a lot of us, that still feels relatively new. That same blank dismissal that Phish gets was applied to the Grateful Dead FOREVER. They represented some hippie bullshit that nobody wanted to be associated with. All of that "When the drugs run out, people realize they are listening to a shitty band" rhetoric was standard. So, now all the same demographic of kids who 15-20 years ago wouldn't be caught "dead" even admitting that they liked a GD song are existing in a time period where the world has embraced them, and I'm sure some of that comes over time with their own heroes signaling to them that it's okay now.
For that reason, the Day Of The Dead box was probably a better introduction to the group than this thing, because it broke down those barriers in a way that showed a lot more reverence and care than I may have otherwise expected from it. You could tell that the people behind it really cared. The VMP release seems like it's targeting the same crowd, but with a less effective delivery. The price is obviously a huge difference and the Day Of The Dead box actually delivered something new. This is old stuff and most of it fairly easy to acquire. Then, you just have Jim James showing up to tell you why it's cool. Oh, and Hunter from Soundtribe, who most people won't even know who the fuck he is.