If you think of it in sequences rather than a snapshot, it is much simpler.
Player B has a pawn for Guild 1 without any influence on the board aligned to that guild and is the Guildmaster. Player A migrates a pawn for that guild and has a location that matches, but has no influence tokens. Player B stays the guildmaster until A gets another influence token.
This is the way I was imagining it:
Player A places a pawn and has 1 Status in a Guild with no other members. But he has no influence markers.
Then Player B places a pawn and now also has 1 Status in that Guild. He does have an influence marker.
So my question really is, does the lack of an influence marker prevent A from becoming a member of a guild when he otherwise would be? And, in the above example, would B become the guildmaster because A couldn't "lock in membership" without having an available marker?
Finally, when A does get an influence marker, I presume he is now relegated to being the journeyman. What throws me is the sentence in the rule book that says you should place your influence marker as soon as one becomes available.
Since you obviously shouldn't have to track membership without markers, then I would assume in this example that B would be guildmaster and A would be journeyman. But if A got an influence marker before B was able to place his pawn, then A would immediately place the marker and claim guildmaster.