Well, I lived in Texas for 20 years and have a lot of Astros fan friends, and they always viewed the team under Drayton the same way we viewed the Phillies under Giles, and definitely viewed him as cheap (the Randy Johnson trade excepted). Of course, the two front offices were also joined at the hip.
Wasn't really even Wade's fault - again, much like the Phillies, ownership wasn't ready to cut the cord on aging legends. And in both cases many of Wade's players panned out for the team that fired him.
I'm sure fans of any number of other teams would look at the Phillies' success over the last 50 years and think we've had it pretty good. Two near-dynastic eras, two fun outlier runs (if you don't consider '83 to be part of the previous era), five trips to the World Series, two rings. A lot of downs in that period too but it's not a track record that screams bad owner or bad culture.
I don't think this Luhnow/Click era maintained any culture from the previous eras. It was a total knockdown to the studs. It was also an import of both Cardinals culture and analytics culture. And of course, it also involved cheating (but then they said that about the Phillies and Charlie too).