I got on the $750 VW package like you, and I feel like I definitely got my money worth. I hung out with the band backstage before one of their shows (instead of a phone call), and it was about an hour all up. Combine that with the box, handpainted vinyl etc. and there was definitely $750 worth of stuff there no matter who you ask.
That's why I feel like this $1k package is pretty ridiculous. Like you I'm a massive fan of both Anthony and the band, but I can't even contemplate spending that much for getting so little. Some bands on Kickstarter charge around that amount to spend the day with you and even give you a guest spot on the album, so a one hour Skype show doesn't seem like much.
Check out Murder by Death's Kickstarter... crazy and extreme rewards like that, and people will happily pay the money. Someone paid $4k to ride rollercoasters with the band all day. But $1k for a one hour Skype? Not so much.