Not saying there's anything wrong with seeing it this way, but from my point of view, I see them falling back on "Jim's Magic Missle(tm)", Binwin being a rather brash warrior, and so on. Those choices fit the PC's personalities. Overall, they seem to be having a lot of fun, so I don't see "problems" that need solving. And what problems I do see aren't often due to suboptimal power choices.
I think they would have fun even if the party was TPK'd...but that doesn't mean they should seek death.
In the case of the last podcast, they made several bad calls that had nothing to do with powers and wound up largely failing.
Well, one thing I saw was the group not using powers they had. Binwin only charged once in the last fight despite picking items that improved his charge. Aeofel repeatedly forgot to use his armor to repel foes. Omin almost never used Sacred Flame, even though doing so could have given much-needed temp HP to Jim and Aeofel (Binwin was cycling temps, and they don't stack).
Jim...well, on reflection, he did okay in that final fight. He used powers that attacked multiple foes (Scorching Burst, Burning Hands)...his dice just weren't rolling that great. His problems are more design-oriented. I think he could use to switch out a few powers to get ones with controlling effects instead of raw damage.
But the interesting thing is, most all of those bad choices fit the personalities of the PCs and made sense from their perspective at the time and have potential role-playing fallout.
To an extent. However, bashing someone back with Tide of Iron is just as in-character for Binwin as "striking brashly". Jim can just as easily use "Jim's Scorching Burst" as "Jim's Magic Missile".
However, I think Omin is the poster child of what is wrong with the group. There were several poor choices, but one in particular stands out. Omin healing himself over capacity was only a roleplaying choice if Omin is a selfish, greedy jerk...which may be the case. But it's not the mark of a group leader, and maybe it's time for the rest of Acquisitions, Inc to stage a corporate takeover.
For me, and others, getting too much into the numbers and only focusing on the optimal choices makes it feel more like a boardgame that we need to "win" rather than an immersive role-playing experience. Now, don't take that as edition war baiting, there's nothing intrinsic in any edition that prevents either style of play.
The thing is, those styles aren't mutually exclusive. It's quite possible to play a character that is both optimized and focused on roleplaying hooks.
Despite setbacks, misses, and some battles being more difficult than they needed to be, it sounds like they were all having fun, even with the fate of Al - uh, I mean Aeofel. That is what matters - the fun. For some "failing" takes the fun out of it, and I can see that. For others, whether you succeed or fail, acting true to the PC and having some excitement is what makes it fun.
That group can make anything fun. But I still sense some disappointment on Wil's part. His character may have died while chasing his oath target...but it was a rather pointless death. By going off on a side quest instead of pursuing the Crest of Melora, he didn't even die questing after his goal. Furthermore, at least two other members were more concerned about treasure and their own skins than the death of their friend ("I promise not to sell your stuff for at least three days"). Only Binwin seemed to be truly sorrowful at the loss of Aeofel.
I recommend that whatever character Wil picks, it should be one that is capable of getting out of tough spots himself. The group plays more as a collection of individuals than a team, and that can be really tough on a group in 4E.
