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.

Wolfgar,

If memory serves, Michael only fails his Personal Story if he receives $5 in one go, so gaining $1 per turn due to the Relationship Business Associates will NOT make him fail hs Personal Story . As to receiving money from someone, I would rule it at my table as "gaining" as any other interpretation is too fiddly and not in the spirit of the game.

Cheers,

Joe

The card doesn't imply memory of the cumulative amount gained so it's got to be $5 all at once.

But I diverge with Joe in that I never count stuff obtained from other investigators as "gained." It doesn't count with cards (for certain PSs), and it doesn't count for getting money with the Business Associates relationship. Either I have to make an exception for Michael's story (which I'd rather not), or accept that there is a minor loophole.

Same as Tibs here!

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.

I wouldn't say that traded money is "gained". Just because for other personal stories it was clarified that you have to "keep" the item needed to pass the story, and of course as Tibs pointed out trading isn't counted as drawing (and, as clarified, keeping) an appropriate card.

I would also allow other investigators to give Michael money after he fails his PS.

Of course, it's very difficult for Michael to actually fail his story and this way of playing it would be helping him further, so you might want to invoke Arkham's Razor on this one