This is great Aaron. Your experience is similar to mine. But from a different angle. I had become enamored with the super serious, righteous U2 of The Joshua Tree, and it took me a long time to warm up to Achtung Baby because I just couldn't get my head around the idea of the band being flippant and dressing in drag and all the rest of it. My mind was very closed. I was also starting college at the time and was seriously distracted by bands like Nine Inch Nails, Nitzer Ebb, Depeche Mode, and all kinds of electronic music. I didn't have time to follow the news about U2 and Zoo TV, and this continued into the Zooropa era. When I saw the video for "Lemon" on MTV for the first time, I didn't know about MacPhisto and I basically said, "Ok, then, Bono has gone full tilt into drug addiction." HA! How naive I was. Lemon is probably my all time favorite U2 video now.
Anyway, I finally did make peace with Achtung Baby and I can legitimately now place it at the top of my U2 album list, in a tie with The Joshua Tree. I think the run of albums from Achtung Baby->Zooropa->Passengers->Pop is U2's strongest period by a long shot. Reading Bill Flanagan's book helped me sort all of that out.
As for CD singles, as a music fan in general I have always adored them. I love b-sides and bonus tracks. I love remixes, especially from the 80s and early 90s. I bought very few U2 CD singles on release day, but you can be sure I have been working to fill the holes in my collection ever since.