While this episode is the most deliberate thus far in its illustration of the results of our central characters' decisions and their dynamics (yielding a bit of a duller viewing experience), on rewatch its made remarkably clear how much foreshadowing was packed in here. Dr. Cruz's analysis of Chuck's condition is practically faultless, with both his and Jimmy's insecurities being its root cause. From the moment Jimmy decided to look past the danger Chuck and his lifestyle posed to himself and others, the writing was on the wall. We can sympathize with him and understand his thought process however, as it's apparent he desperately craves the approval of his older brother: a paragon of justice and in essence his savior (see S1E3).
The tedious consultations serve to illustrate the closing of a vicious loop that plagues Jimmy throughout the series. He utilizes underhanded methods to compensate for the universe's slights against him (as he sees it). This way he can prove to Chuck that he can be a legitimate lawyer and dutiful citizen, thus repaying the debt he owes Chuck for giving him a second lease on life. Unfortunately, this "chicanery" always yields unintended consequences, and never gives Jimmy the satisfaction he impatiently yearns for. It's as if the mistakes of his past life bleed into his new one in the form of karmic retribution. This premonition is almost palpable for Chuck, manifesting in his condition and his compulsion to insulate himself within his "space blanket".
Kim's role as a mediator in Jimmy's relationships with Chuck and Howard is also made more apparent. She urges him towards more noble pursuits where she believes he can thrive and satisfy his brother's aspirations for him (ie. Elder law), and makes an effort to defend his honor when Chuck and Howard antagonize him. While her initial intentions are certainly respectable, she sees herself become an enabler of Jimmy's self-destructive tendencies while also being corrupted by them herself (symbolized elegantly in their smoking scenes). Their relationship is one of the more beautifully tragic I've seen in television, and this episode explores an interesting aspect of it.
We also see hints at the depth of Mike's character. For unknown reasons (as he said, "Nobody wants to leave home,") he was forced to abandon his life as a Philadelphia cop, and now lives a modest life as a parking booth operator while keeping careful watch over his estranged daughter-in-law and granddaughter. At the episode's conclusion his past literally comes knocking at his door, and it seems like his connection with Jimmy might come in handy.
While not the most riveting first watch, it becomes much more engaging with subsequent viewings. 8.5-9/10.
