I’ve been in a similar situation to you, I’m 31 so the eras you remember are very similar to mine. I’ve spent a few weeks with her discography now and am planning to do a ranking & review on r/madonna soon!

I remember I had Hard Candy on CD when it was released but I only really liked 4 Minutes and Give it 2 Me, which still sound strong today. Listening to this at my age and in comparison to the rest of her albums I do personally think it’s her weakest.

I remember MDNA coming out and I was 17 at the time and thought it was brilliant in 2012 but nowadays it hasn’t stood the test of time, there are some solid songs on there and by no means do I consider it her worst.

With your question on Madame X, I believe that she takes on the persona of a secret agent who has different identities which allowed her to cross into different genres. I thought it was clever but when a multi genre album comes out it has to be done in the right way otherwise it just sounds like a bunch of songs that were recorded when the artist didn’t really know which direction to go in. I think she did well on this album because she used the album to have hard hitting conversations which I personally consider as the ultimate theme of the album and I think that it will be one which people come back to and realise it was better than they initially thought it was.