WARNING: CONSTRUCTIVE CRITICISM:
"...As you know Bob" is a horrible way to make allusions to the state of the AH world. No, no no. Have you read the Man in the High Castle? There is one part where this mistress of this one character tells him about the Grasshopper lies heavy AH novel as a way to illustrate to the reader how the Axis won without sounding like one big info dump.
If Bob already knows what happened to, say for example Cuba, then why does Character Y have to tell Bob this info in such a blatant, info dump?
Character Y, reading the newspaper, could remark to Bob:
"Hey Bob, apparently those Cuban pro-democracy protesters are at it again. Can't wait till we send in the US army to squash 'em."