Dale was finally moved when the team was already losing - Rik, Jax and Mullin. And Dale had postured about money and got himself in a bit of bind with his agent that forced things along a bit more than he might have wanted. Had Rik stayed then they would have spent a bit more to keep Jax, not traded Dale and would have taken another shot at it. And they were old.
You don't bail on value right when your in-prime team is starting it's 4-5 year run. That would be akin to trading Dale or Reggie in 1996 or 97. And at the time many posters here at PD would have backed that view given the disappointment of not repeating the ECF runs. In fact they DID TRADE VALUE in 1997 to get a young player coming up - Jax for Rose. This was a big part of why they failed in 1997, and they recognized that when they traded to bring Jax back.
So let's slow the roll on the whole "obviously you trade while a guy has value, it's the smart move". It hasn't been, not when the core is all young and in place. You don't panic in a weird year or a weird 2-3 months. You must have vision for the situation that's only just been assembled in the last year.