My tale of discovering David's music has some similarities to yours.  After about 1980, my parents decided they couldn't afford cable TV anymore.  We weren't "dirt poor," but we were moderately poor, and two of us had violin lessons, which were really expensive.  So a decision got made.  But in the summer of '86, they must have gotten a good deal because they got cable TV back just for that summer.  This was my first and only experience with the mythical "MTV" that many of my friends discussed all the time.  That summer, Boomtown was a video in major rotation, and I loved the song.  It was also perhaps my first experience with music that criticized the yuppie culture of that time.   We lived in such a small town that we never really saw that culture close up, but the images from the video remained in my brain and made some more sense years later. 

I missed Bedtime Stories, but I think I remember a magazine article about it or about Triage when they came out.  Probably Triage.  A lot of time had passed, and the article made reference to drugs in a way that put me off getting those at the time.  But I was really taken with Kevin Gilbert/Toy Matinee music, and once Sheryl Crow's album came out, this led me back into discovering David's stuff.  Got Bedtime Stories and Triage perhaps in 1994 or 1995, and I remember Triage, in particular, making a deep impression.  Loved it:  the production, the twists and turns in arrangements, David's lyrics, and the vocal melodies were all outstanding.  I was officially a "fan." 

I was aware of Grace of My Heart and loved the "Boat On the Sea" track.  And I got the "Hurly Burly" soundtrack, loving "Petra's Ultratheme" and "Black Mamba Kiss."  Didn't care for the movie all that much, and I normally enjoy Sean Penn's work. 

Scanned the internet for any "next" releases, and that quite obviously led me here at the time of "A Fine Mess," which was also outstanding.  Although sprawling, some of David's very best songs are there.