I don't think Bogey and Clarkson were bad deals....I do think it was terrible management to not move at least one of Conley/Bogey/Clarkson for a different type of player. These guys all helped us, but we had a surplus of certain skillsets and nothing in other areas. But to name a few guys that I feel confident we had the juice to get at different points:
Covington
Powell
D White
Smart
Brogdon
Hart
Markannen
I think there was also a possibilities we put together more assets to go after a player like George/Butler (who I think were both moved twice during this period). I'm not gonna say we could for sure get them, but having more ammo in trades is always better than less. Our investment level into the defensive wing situation was paltry. I do not think Conley prevented us from preventing us from upgrading, but I also think Conley exasperated the problems. If you badly need a wing bc you have Don + Gobert you need one even more if Conley is sharing the court with those two. If it seems difficult to find the perfect guy to fit, I would generally not advise getting guys that make the problem more extreme.