After happily running 3E and 3.5E since 2006, I read the 4E PHB in 2008, realized it was not the system for me, especially as my play was almost entirely play by post, which would have required a lot of additional work to make 4E combat work well. But the system of sanding away most of the variety of pre-4E D&D to get it all balanced -- while understandable -- meant that a lot of the stuff I liked was gone. (Nowadays, I also play in person and via Discord and 4E would probably more doable, but I'm still not convinced that its tone and specific flavor of game would be for me.)
A few years in, when 3Eisms were starting to get me down as a DM -- I got tired of the arms race with some of the character-optimizing players -- we switched to Castles & Crusades instead, which has the 1E tone I love and a lighter-than-3E but still wildly compatible system. But after a few years, some of the quirks of C&C started to bug us (no one ever really got the SIEGE engine and for whatever reason, my players couldn't get their heads around skill checks without skill lists, to the point that I just had them refer to 3E skill lists when they were confused).
So in mid-2018, after reading a rave review of the Starter Set, I picked it up for a song, read through it, was amused at how much of 5E was refinements of the way Castles & Crusades was doing things, and that it answered out issues with C&C and offered the folks who missed the character build minigame stuff to do, and pitched my players on making the switch.
(I had previously played from 1979 through 1984 and then took a looooong break where I was just a reader, not a player, during the later years of high school, then college, then bopping around doing a bunch of jobs in my 20s, before running 2E games online via Java chat rooms in 1999.)