Wtf.  No.  She should be back at work since her youngest started first grade, regardless of SS's injury.  I would be pissed.

So.. the child that has basically ignored you and his dad now "need" help?  and "WE" (please confirm you really mean your husband's money.. not what you work for). will be helping?

I have no problem if they want to have a parent at home with the kids if they can afford it... but right now.. with him not working and getting a lower disability pay?  It is ABSOLUTELY.. time for his wife to go out and make up that difference.

If it is a couple thousand a month? she should certainly be able to pick that kind of job up.. and SS can take care of his kids as a SAHP.

Yes.. bring it up.. bring it up proactively.

It's one thing to help in an emergency.. but before it becomes another month down the road.. dad needs to suggest to his son that his wife needs to re-enter the workforce because she is fully capable of earning enough to cover the shortfall his situation is causing.  

No way should you guys be bankrolling this any further.

My first question was going to be whether he could take care of the kids. If he couldn't, then I could see the argument of her not going to work if child care + his disability care costs would be on par with her salary. 

However, it sounds like he CAN take care of the kids and himself so she COULD work. Additionally, since it sounds like he isn't getting any disability coverage from his job (is he even still employed?). Does your SS have the option of taking on another job to bring in income? That could get sticky depending on what insurance he currently has, how his disability protections for his job are laid out, etc.

Absolutely speak up about it. Your DH shouldn't be fully supplementing his son's income (and you shouldn't be contributing at all unless you really want to). If your DH doesn't want to stop entirely, ask him to pick a reasonable bill that he is willing to cover. Maybe he can cover their electric or cell phone bill, or send them monthly gift cards for groceries. I'd be super concerned about him just sending a check because there is no guarantee that what he is giving them money for is actually being used appropriately, which just means they may end up worse off than they are and your DH will want to dig himself into debt to help them out of the bigger hole they dug themselves into.

If SS is able to stay home with the kids, then his wife should go to work before your husband supplements their income.  They'll still have a parent home with the kids and no daycare costs. Plus it doesn't seem necessary to me to have a SAHP to school age children if it isn't affordable.  We're not talking a couple months, either - this is a year.  If his wife doesn't have the earning capacity to replace SS's income and they need that whole income to pay the bills, then I can see your husband (not you) helping with the difference or a part of it.

I would absolutely raise it with your husband.  I would be uncomfortable shelling out $$ at a time when you need to be preparing for retirement, and there's no way I'd be working while giving $$ to SS and his wife when his wife was not working outside the home and SS was not earning anything he could without risking his disability income. That is the recipe for resentment. 

I'm ok with helping out in an emergency. But, once through the emergency, I'd expect the couple to be doing everything they can to take care of themselves. Why the entitlement to continue to be a SAHM when her family's income is reduced? How is that anybody else's problem to prop up? And what grownup with three kids and any self-respect at all would want to rely on a parent for living expenses?

Is your retirement savings sufficient? If it is not, that extra couple of thousand needs to be going there.

If your DH insists on helping somehow, decide what that one thing is, and stick to it.

Why aren't her parents chipping in?  

I think we all are in agreement: Step DIL needs to get off the SAHM bus and get a job. You wrote:

"We are now going to help supplement his income ( will be several thousand dollars) "

Which leads me to assuming that either you put both your monies into a common pot and mingle them, or your rightly feel that marital funds belong to both of you.

Did you discuss this prior to doing it? When did this start?

More importantly, in answer to your question - no absolutely DO NOT send one more check until these things have been discussed and agreed on by everyone. If you are involved in SS's finances to the point your retirement funds are being depleted, then you certainly can be involved in limiting the amount, and you certainly have the authority to mention Step DiL getting a job.

I would not be funding this, except as a limited loan.

There is no way on this EARTH that I'd be supplementing someone's income so that they can afford the luxury of being a SAHM. Time for the dear lady to find a job to support her own family. The kids can surely go to afterschool care, right? I'm sure they're also capable of doing chores around the house to help out. 

The pair of them need to work out how to survive the injury and the lack of income without expecting their parents to pony up. They are grown-ups and parents, time for them to set an example.

You are completely right. Why isn't he staying home with the kids while she works? There is no reason for you to be giving them money. DH is being suckered.

Just to go further.

I read this as her DH was sending money to supplement her SS's income.  Which led me to believe that he is getting some amount of "disability" payments.. probably from his company's LT Disability insurance provider.  It probably covers 50 to 80% of his salary for long term.  

It's not fair to put your hand out to people when you have options within your control to take care of yourself.  His wife IS capable of working outside the home.  The kids are old enough to be self reliant...and not need a ton of active oversight.  The oldest in middle school should be capable of helping to care for the younger kids .. you know .. pull together for the good of their family.  I'm not saying the kid has to go get a paper route to pay for food..lol.. but helping with extra chores.. staying home instead of running with friends as much.. when they are needed to help a parent with their younger siblings.

I don't have a huge problem with SS coming to dad and saying.. Hey dad.. I just found out I will be out of work for a year.. Betty is going to look for a job to make up the difference in income I am going to lose.. but do you think you could help us cover the gap for a month so she has time to find something?

Then.. if "betty" has actively been looking.. but it stretches to a 2nd month.. I think it's fine for dad to say.. I can help one more month.. but after that.. you will be on your own.

That may mean they have to make some choices about their lifestyle.. maybe kids activities are cut.. maybe budgeting is more stringent.. maybe Betty gets herself employed.

Having one person stay at home is a luxury that many families cannot afford.  SS's Wife has been fortunate to have that time with her kids.. but it's not realistic for her to continue to stay home when her husband is unable to earn his full salary.. they have two choices.. cut their spending to match his "new" income.. or figure out how they will cover those costs.. without asking others to do it for them.

There's no reason that she can't work. They really have a lot of nerve expecting a hand out while she sits home.

My SD (has never worked) and her husband blew all of their stimulus money (3 kids) on luxury items and I wouldn't give them a dime.

Nowadays, in most families, it takes both parents working to make it.  But often, one works and the other stays home with the kids.  So, if SS is home to watch the kids, drawing 60% of his pay, the wife should be working to make up the difference.

"honey, we sent the one check to help them out. hopefully she will be working soon and contributing as well. We cannot afford to pay him to stay home and at the same time she's doing nothing to help out. Do you think they need help writing the ad to sell the boat, they won' be using it now with him being so disabled and her not working."

Your SS & SDIL are taking advantage of you & your DH, this isn't reasonable. I get wanting to be a SAHM, I was one for nearly 3 years, but when the need arises & you can't afford it anymore? Time to get back to work. Their kids are in school as well so there's really no need for SDIL to be at home anyways, unless they could afford it, which right now they can't. Why did your DH agree to do this? How is it impacting your finances & future? Not to mention the precedent this is setting, how long are they going to milk this for?

When people have kids they are the only ones responsible for those kids. Sure, receiving help in an emergency is one thing, but this?? Big fat nope. I’d be disgusted if I was you, your SDIL has a responsibility to provide for her own children. If her DH is out of commission then it falls on HER. They are her dang kids. I can't imagine being entitled that way, I’d have a come to Jesus with your husband, this is totally unreasonable and not at all ok.

Works comp or disable from his work.  I am sure he's well enough to take care of kids who are 10 years old and older.  The older kids must pitch in with cooking and cleaning. The wife must get a job, real 40 hours a week job,   If then there isn't enough money maybe then I would pitch in.  If it doesn't put you in money trouble.  
I would not give up my retirement money for SS. Only what you an afford.

SS must tighten his belt, sell second car, get ride of toys,as  boat, jet skis. Ect.  Stop unnecessary expenses as cable TV. Netflix cut down on cell phone.  Eat a lot of pasta, chicken eggs,  no fast food, no MickeyD.  There  other things that can be cut out. Cable, cellphone no eating out can equal $500 a month or more   It's not fun. But that how life goes. 

Kids are school age. She should work while they are in school. Who's she staying home with? Not with kids! I understand SAHM iIf kids are home but they aren't.