Your post here really just resonated with me and took me back to 1992. Like you say, Madonna hadn't released anything since The Immaculate Collection in 1990, and information on artists and New releases was so much more difficult to find out.
I was only 16 when The Immaculate Collection was released. As far as I was concerned, and was led to believe, a greatest hits package was an artist's way of grouping all their best work together and then signing off. I was under the impression that Madonna, my favourite artist, had called it a day. Seems crazy to have thought that now.
The release of This Used To Be My Playground came out of nowhere and the track absolutely stunned me when I first heard it. She was back, and The Immaculate Collection had not been the end. The long version became the default listen as I found the single version too short. I found the music to it beautifully haunting, and on many occasions, then and since, there's been a lump in my throat by the end of the song. How utterly raw with emotion it sounded, about someone looking back at their childhood, just at the point when I was on the brink of turning 18 and leaving my childhood behind.
Yeh, it unfortunately appears to be a forgotten and overlooked song, but not with me. Like the Erotica album which followed not too far behind, it arrived at a really huge time in my life. Pretty special.