So, I've been in a few games with someone playing Michael with his Personal Story, and frequently the "Business Associates" card pops up with him as well, leading to the following headache.
Business associates lets you gain a $1 whenever your partner gains money. Notably you can't really use it with trading money between investigators, or else you'd get stuck in this weird munchkiny infinite money loop. Fine so far.
Based on this, my group has run with the idea that money acquired by trading isn't "gained", and therefore 1) does not count towards Michael's Personal Story failure condition and 2) that if Michael does fail his personal Story then other Investigators can just give him money instead. I think this is wrong, but I thought I could at least get some confirmation from the forum before pouting about it.