I don't know....this sounds like more trouble than it's worth. It's almost like babysitting the entire time....doesn't sound very fun to me.
If I'm backing someone, I basically trust their play and judgment. If I questioned any of it....it's not worth my troubles.
I would only do this if it's an extremely positive EV move. Also, I would get things down in writing before you proceed with the action. It doesn't sound like you are that close to him.
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