The drafting and development failings - that ship has sailed and we can only hope Barber (a Klentak/MacPhail hire - technically their only one for that job!) and Mattingly (who still kept the Driveline guys) are a better answer.
But the pivot point for this group was 2019, when they realized no help was really coming (mostly from the Hamels trade) and decided to become a veteran team (and at the expense of the current best player on that list from 2011 to 2021 too). The past two seasons were another pivot point, as the prospects still failed to arrive (or flopped) and they continued to proceed full speed ahead. Which in some ways is fine, I neither wanted nor expected a full rebuild let alone a tank (Oakland and Pittsburgh and Cincinnati aren't tanking to rebuilt, they are tanking to make profits, and other teams - most notably the Phillies - have shown the Astros formula isn't easily repeated).
But thus far Dombrowski has shown no facility for actually tweaking and improving a major league roster, which is the one thing he did successfully in Boston and the one job he had here. Really, he hasn't even tinkered (no trades), and last year's team was basically the same as 2020's. Of course he inherited a much better foundation in Boston (so much so that his predecessor probably shouldn't have been fired).
They may not be this bad but it seems pretty unlikely we'll be sitting here in October saying, "wow, remember how negative we were in May? Dombrowski really showed us!" And it's pretty easy to see the flaws: the millions of DHs, the mishandling of the left side of the IF and the lack of a CF or lead-off hitter.