GregVsMatt

Promo shows are meant to be short - a few new songs and one or two classics

I think the "insider" meant she finalized that work in the last few weeks, probably green lighting things, final touches, cover, whatever. Not that it was done 100% just in the last few weeks.
Proper behind the scenes work on the reissues has been going on for years now supposedly or so they said other "insiders".

I think a promo tour is supposed to be short and focus on the songs that are new, 1 or 2 old songs is enough imo.
Don't Tell Me promo tour and American Life promo tour are just perfect. 

I don't think that's the case. The anniversary was July 2023, if anything was planned it would have been announced and ready to go with pre-orders at least two months previous to that. Even if it was planned for later, it would have come in the Fall, vinyl pressings take months in advance and they're not wasted, just delayed (that's what actually happened with the "Madame X Tour" triple vinyl, they just delayed it for some weeks).
There was nothing coming for "Madonna 40", simple as that.

I'd be interested to see evidence of such a purchase 

I'd be interested to see evidence of such a purchase 

1989 USA sheet music artwork 

1989 USA sheet music artwork 

1989 USA sheet music artwork 

Yes the single release was 24 October 1989 and the video shoot was the following week 

I guess they would follow the route of the US 1989 single if anything, repeating content when they already put those two live tracks on the "You'll See" and "I'll Remember" digital singles would be weird (the "Live To Tell" live track on the 1995 UK single was an edit cut to 6 minutes, they could use that one but I doubt it). Though there's nothing left unreleased on streaming that they could use, really. I can see:
01. Oh Father (Edit)
02. Oh Father (Album Version)
03. Pray For Spanish Eyes
And this cover adapted:

Again, I can't see "Oh Father" at all, sadly, though I'd love it. And that amazing video needs an upgrade - as many others of her on YouTube.

They were designed by Grant Shaffer who would meet with Madonna and the director (in this case Bobby Woods) and they would map out the video - he would have just been told 'Vogue' and also you'll notice M's hair was drawn down. The story boards would sometimes end up in Icon (Rain, Bedtime Story etc) at the time too 

Also was in the story board in Icon  

I noticed it back in 1992 and assumed it was a nod to the Vogue lyrics in the song too

Also was in the story board in Icon  

Also was in the story board in Icon  

Also was in the story board in Icon  

Also was in the story board in Icon  

Also was in the story board in Icon  

I noticed it back in 1992 and assumed it was a nod to the Vogue lyrics in the song too

Also was in the story board in Icon  

They were designed by Grant Shaffer who would meet with Madonna and the director (in this case Bobby Woods) and they would map out the video - he would have just been told 'Vogue' and also you'll notice M's hair was drawn down. The story boards would sometimes end up in Icon (Rain, Bedtime Story etc) at the time too 

Also was in the story board in Icon  

Also was in the story board in Icon  

Nope - you can find every live performance referenced here https://www.setlist.fm/setlists/madonna-bd6bdbe.html