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@dallasreds
I think there is no difference between Wealthy Rogues appearances in the Caves and in island levels. We just encounter them in the Caves a lot because these are the levels we primarily play to grind right now. :p
BTW, just for the sake of it, my current ranks:

I marked each class that is closest to rank up for each bird, these are the ones I play with in the Chronicle Caves for some bonus Mastery:
Witch (8 -> 9): 2135 to go
Guardian (10 -> 11): 8369 to go
Rogues (10 -> 11): 9980 to go
Mage (10 -> 11): 12552 to go
Pirate (10 -> 11): 18974 to go
Other important classes:
Paladin (12 -> 13): 32831 to go
Wizard (14 -> 15): 36395 to go
Sea Dog (7 -> 8): 19548 to go
Spies (12 -> 13): 33239 to go