I guess before you decide whether its a hill to die on, you need to lnow how you would know if DH bought something.  If he has a separate charge, or if you don't see the expenses, then you won't know.

Personally, I believe in allowances, a fair amount whether they do chores or not with the firm proviso that it covers EVERYTHING.  My mom did this with me and it successfully taught me budgeting, delayed gratification,  judging quality and the value of working.  But, she was strong enough not to give in and pay for other things.  I tried to do this with our 5 but Disney Dad was incapable of saying no so I wasn't so successful with our kids.. 

I would stop allowing things to be purchased at my house...if SS wants to take "his money" to BM's house, that's fine, but that doesn't mean that other money is spent on things for your house. If SS wants something at your house, he can spend "his money" on it. 

I think the concept of earning money for chores has a great value behind it. You want something, you work for it. It teaches kids to save up if they want something big. It is HIS money so he should be able to spend it how he chooses but the problem is your DH. If SS wants something at DH house, he needs to use HIS money and DH needs to enforce that. 

Ah yes, this used to happen here too.  It drove me crazy after birthdays or xmas when they would take everything we gave them to their moms and we'd never see it again.

What my DH does for allowance, is he keeps a running totally of their money. But he doesn't give it to them in cash.  So when they want to spend it, they have to do it with him around.  Works better than it used to. 

The problem isn't giving him an allowance, or him taking his money to BM's house.  It's *his* money, and if he wants to take it to BM's house, I don't think your DH should stop him. As you've noted, the problem is your husband not requiring SS to use his own money to buy the stuff he wants.   Different families treat this differently.  Some require kids at that age to start buying their own electronics, clothes, extras, etc., and other families allow the kid to save his money and still pay for the extras.  I grew up in a family that could easily afford the extras, so my parents bought them and I saved the money I earned.

If your family is struggling to pay bills and you're doing without while DH is buying luxury items for his kid, while the kid has the money at his other house to buy it himself, it would be a hill to die on for me.  If not, and if it's DH's money and not your money, then it wouldn't be.  If you and your husband have joint finances, then I think you should have a say in how the money is spent.  

This is a DH problem - DH should be telling him NO, you can't buy that because you have no money, you left it at your mother's house. Then SS would either leave some at yours or take some back and forth, after a few times of not being able to buy things.  But you know this is a pointless argument, because you can't make SS leave his money there, what, will you shake him down every time he leaves your house? 

Work on your DH's follow-through, not on any one individual issue.

This is a DH problem for not making SS spend his own money. A practical solution would be for DH to set up a bank account with SS and they BOTH have a debit card to it. If SS doesn't bring his money over from BM's and doesn't have his debit card, then DH can whip out the debit card and pay using SS's money. It still coddles SS, but at least it would be HIS money being used.

You will just have to raise holy hell with DH, and I think it would be fine to do that. I don't think it would be wrong of DH to buy SS the occasional gift/new thing, but it should be because he WANTS to, not because SS asks for it. 

This wouldn't be my hill to die on. What would be my hill to die on is if DH were racking up debt, couldn't pay his share of expenses, wasn't saving enough money for retirement, didn't have funds to go out on dates with you, etc. If he wants to spend his "fun money" buying things for SS, so be it. However, once it becomes an issue that directly impacts your mutual livelihood, you need to take a big stand.

I am ok with kids getting allowance. What I am NOT ok with is kids taking it to the other parent's home. Doesn't work that way.

*now of course he could steal the loot from your house THEN tell you 'someone' stole it THEN dad could double dip to make up for the pretend stolen money because the case is still in court*

based on true story.

My problem here too.  All of YSD's gift cards and money are hoarded at BM's. She has no reason to use any of it because BM and DH don't require her to. I say at almost 15 if she wants special toothpaste that's 3x the cost of basic toothpaste, then SHE buy it. I wanted special shampoo at that age, my parents had me use my allowance so special things - there you go. I learned how to budget and buy things for myself.

But hahahaha, I mention anything that sounds like "parenting" to DH he either shuts it down or ignores it, so I just ignore all of it.

IMHO chores should neither be compensated for, nor should they be used as punishment.  They are the child's required contribution to the home and family.  If they do them without complaint, great. If they don't, they learn to live with a state of abject misery that will soon get them happily working on chores.

Allowance IMHO is tied to age, behavior, and school performance.  They get it unless they pull any behavioral crap.

Interestingly, as an only child in our home, we gave SS an allowance which he never did anything with.  He was always with his mom and I and we paid for everything. So by the time he launched, he had bank in his account.  He still has not spent any of it and has saved notable funds from his salary over the past nearly 10 years.  He has a ton more in the bank than I had at his age.

When we are together, we pay.  He does go nuts on Christmas gifts for his mom and I and the whole family.  He gets that from us and from my parents.

Step life in general is a hill to die on. 

We considered using the app Rooster. It keeps a running total of allowance. They can keep it there to save up for something or enter in purchases. They have to have a memo. They can cash out or have a parent hold onto it. That way they can't say that they don't know where it went.