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Short question:
For example, I field 2 Jokaeros in a Warband:

1st roll: +1 for having 2 Jokaeros
2nd roll: +1 for having ...
...

or

1st roll: +1 for having 2 Jokaeros
2nd roll: +2 for having ...
3rd roll: +3 ... (if I roll 6 or double)
...

/Edit: oh and sorry ... wrong forum

There's only one roll, no matter how many monkeys you have. If you roll the 6 result to get extra rolls, the per monkey bonus still applies, so having too many monkey's will guarantee you get nothing.