Would this piss you off?
My husband(SO) has a side Business and makes good extra money buying and reselling from estate sales. He wants Step brat to get into it. The “plan” is to educate and bring Step brat to estate sales so step brat can pick things out to resell. Sounds all good BUT I know step brat. He’s lazy as shit and will not do any of the work that goes into reselling the items. The reality of what will happen is SO will front step brat money as he never has any, step brat will buy a bunch of stuff and SO will end up doing 98 percent of the work to resell it BUT will let step brat pocket all the resale money. Then STep brat will end up bringing all the money back to BM house to spend. Oh and at least half the shit Step brat buys he will end up keeping not reselling and that too will end up over to BMs house. Why do I care since it’s not my money? Because we are not made of money and step brat blows though money like it grows on trees and just wants to buy to buy. This kid can spend $70 in the dollar store on worthless junk half of which he will lose or break within a few hours. Anything good he buys ends up at BM house never to be seen again. I just see this as another way step brat will be just handed money to blow on crap or stuff for BM house. Would this bother you?
It would worry me
Past behavior speaks for itself. If he hasn't been responsible with money in the past and hasn't shown any progress in changing it then it's a pretty safe bet you'll see more of the same. If you aren't involved in the business and have no financial investement then its kind of hard to say anything to discourage it. Still its frustrating when you can plainly see what the future result is going to be and watch your SO blindly go with it. That would make me mad.
I would recommend talking DH
I would recommend talking DH into starting out with small amounts to piss away and let the SS earn his way into bigger "investments" in this stuff. You can't teach without a little failure but you can't just hand over a wad and expect him to get it right away.
Yes it would bother me if it ended up being a hand out but knowing this, your game plan is to minimize the loss to the family budget.