In my opinion, her recent years team is a bunch of Yes People and that's the type that can do serious damage to one's success. A perfect example is the Aretha tribute speech; hours before she went to the MTV, she posted an Instagram muted video where they were doing her hair, make-up, etc, and she was reading what she would say (the paper with the speech text could be seen). Now, how come no one told her: "M, I believe that your speech is full of good intentions, but as it is it sounds a little bit self-absorbed, it's too much about you and too little about her. Maybe you could balance it more so that a backfire scenario won't happen."? No one told her this? Or maybe they did and she didn't care? Who knows. The truth is that it backfired badly and it did her image no good at all. One can say "who cares, she survived all of that, etc", but the legacy of these poorly planned situations (Aretha, Eurovision) is nothing but negativity. Madonna goes there, do her stuff and obtains little to none positivity in the end.
And I find it funny that some fans make no big deal about the missing opportunity that was Eurovision and are now focused on Pride in NYC as if such event will do anything for Madonna (get the general public back, give her a good public image, etc). Will it be broadcast for 200 millions of people of different nationalities at the same time? I mean, for all I know, Pride is something just local and isn't even broadcast, am I right? The only events on the league of Eurovision are the Superbowl and mayyybe the World Cup and Olympics closing. As @Kim said, this was a once in a lifetime opportunity, so every scenario should have been thought for it to be a success; but, to be frank, we are very lucky that a 2015 Brits situation didn't happen again, cuz God knows what a video game final level the whole thing looked like: 60yo, innumerable stairs to go up and down, an eye patch to not see straight, heavy clothes to limit the moves, accessories asking for a wardrobe malfunction, a lifeless version of a classic that everyone loves, a non-single, I repeat, a non-single to promote a new album and a featuring guest that no one knows in Europe and that she had to take care for how much lost he looked like. It's amazing what an Herculean task it all was and how in the end the vocals were the only thing that went wrong. Madonna is a pro, there's definitely no doubt about it.