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dD_ShockTrooper

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I don't want to talk about the usefulness of doing so here, just the fact that you literally cannot do so. Is there some way to mark a checkbox so that the AI will send you condottieri deals even if they think an AI in your position would never accept? The current system is really good for a player who doesn't want to be spammed to death with terrible deals and misclick into a bankruptcy, but sometimes I'd like to be able to take out a stack of loans for some overpriced 20k foreign troops. The only time an AI ever offered me condottieri it was free; this AI had a track record of showering me with gifts and subsidies and this was just one part of that.
 

bokorthedust

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If you have positive income and can afford it (and the other conditions related to not having truces are also fulfilled), the AI offers condottieri plenty of times. I rarely accept them outside of the early game when I'm playing a somewhat affluent OPM, but they regularly offer it in my games.
 

Nostalgium

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Condotierri is one of those weird mechanics that doesn't really fit into the puzzle, I think. The fact that you can't state interest but only accept offers puts it in the same place as selling provinces.