NOTE: In S2E10, Sophie invites Susie over “this Friday”, then Lenny invites Midge to see his show “this Sunday”, then we see the Friday visit occur. Because of this, Lenny's invitation (and the Sunday in question) must fall within the same week at the Friday in question. We know that the day on which Lenny gives the invitation is in November, because earlier in the same sequence somebody refers to a gig they will be doing “for a week in December”, which would not make sense to say if it were already December. However, on the Sunday when Midge goes to see Lenny's gig, Shy calls with a job offer to go on tour in “two weeks”. If that were true, it would put Midge in Vegas over Christmas time, and there are no Christmas decorations visible in any of the Vegas sequences (S3E3 & S3E4). The only Christmas references which are made in season 2 or 3 of the show are at the USO show in S3E1, so it would make sense for this sequence to occur later, close to Christmas. Furthermore, the slogan “It's the Sixties, Man!” is debuted by Abe's communist friends in S3E2, heavily implying that it is January by then. Therefore, I have chosen to make the assumption that either the tour was delayed by several weeks off-screen at some point, or Shy simply misspoke, either of which is plausible given Shy's temperament.
NOTE: There are numerous internal contradictions and inconsistencies in the order of events depicted in S3E5 and S3E6. The only way to reconcile these inconsistencies was to make two assumptions: (1) that the order in which the scenes are presented are not quite the order in which they occur, particularly with regards to intercutting between Miami and Florida, and (2) that offscreen, Abe and Rose somehow managed to wiggle out of seeing Midge on the night they initially agreed to see her, pushing it back further and further until it got to the second last night and they couldn't back out of it anymore.