Letting the cake bake is not only an ok strategy..... It might be the only option since the free agents mostly either stayed in good situations with their own teams or saw good opportunities on other teams and got overpaid.
Reading through everyone's comments, I think this single statement by fish hits the nail on the head. NAOS, I'm sure your question was really just meant to spark a great conversation-- and it created one of the better threads in recent memory, imo-- and not imply that the FO hasn't done its due diligence in terms of pursuing free agents that would add the depth needed to make/contend in the playoffs. But the implication is there nonetheless, and is kind of at the heart of the point I want to make.
Personally, I'm of the belief that DL & Co. have no misconceptions about what they are working with here in Utah. We've all heard them tell the media they are going after free agents aggressively, and feel like they have a "story to tell" about what a great place this is to play and live, the legacy of the team, etc. That's nice, and I love it here myself, but... they aren't fools, and they know exactly how this franchise compares to those in other markets-- especially in the eyes of the players across the league. So what do they do with that? Well, to say that they're ambivalent about making the playoffs is to infer that they don't even bother pursuing and making substantial offers to <insert your favorite free agents>-- that they give up, or make half-assed inquiries. Since we're speculating about conversations that may or may not be happening behind the scenes, though, isn't the more likely assumption that the Jazz reached out to the agent of every player mentioned in this thread so far, and got a flat "no thanks"? I think so. And I think every fan in this market with half a brain has to concede that as the most likely scenario. I also think they're doing literally everything they can, and rather than signing the Kawhis of the league, they find themselves mining the D League for another DMC, hoping to sign another Trevor Booker, etc.
It may be frustrating as a fan to accept we can't blame a lackluster free agency period on anything other than being the ugly girl hoping for a date to the prom, but shouldn't we be used to it by now? Some of you have bought your pretty little dresses and had your hair done for weeks now, apparently. I feel for you, and I hope you are cool with watching reruns. The really raw truth here is that DL knows what he's working with. Fortunately, he's the kind of guy that likes this kind of challenge, because he's seen the puzzle get solved in other places, and he is convinced he can do the same. To which I say, Thank God.