The last time a first pick Daily Double happened pre-Holzhauer was on February 28, 2019, during the All-Star Games tournament, just over a month before the Holzhauer run. 11/12/2018 during a Teen Tournament also had a first pick DD. The last occurrence during regular play before that was on the Season 35 premiere at the beginning of that season. That's over 130 regular play games without a hit, so that's a pretty significant event for that occurrence, even though only about 20% of all rounds didn't start with a top row pick from my research.
Well, we're already up to eight automatic qualifiers for the next Tournament of Champions, and so far this season, there have only been four shows without any contestants will have qualified. We didn't have the Teachers no College Tournaments last season, so I'd expect those to be coming this year (for the Feb. and May sweeps, or perhaps even in primetime), and it's possible by next November, we could have another ToC if we get enough qualifiers by the end of the season.