Okay, so H and I are doing Dave Ramsey's TMM. We are on baby step #2 and paying off debt, but instead are currently putting our snowball into savings to stockpile until after baby is here.
The next debt in our snowball is one of H's student loans that we will pay off after all of the medical bills are paid for. However, we were talking with BIL the other day and he reminded me that H has a small debt to MIL from almost 5 years ago when he was out of work for 9 months. I asked MIL about the amount of debt he owed her, and she said that she wasn't even sure how much it was. She thought it was something like $1,200-$1,600, but she isn't worried about getting paid back for it.
I've talked it over with H, because I personally don't want any debt owed to any family member at any time and I really want to just give her money for this debt and be done with it right now.
Here is his deal with the debt....
It was for car insurance that MIL paid for him for 2 out of the 9 months he was unemployed, and a homeowners insurance deductible when a storm zapped our central air unit while he was out of work. He thinks the total was $1,200 (she isn't sure what it was).
Now, BIL has lived with MIL forever. He's 25 now, has his own full time job, makes really good money, but spends it like it's going out of style. She has paid for his car insurance since he turned 16, and just 5 months ago he finally got onto his own plan. He doesn't buy groceries, doesn't pay for any utilities, and is constantly asking his mom for money because he simply chooses not to save. In May he got into a major car accident from driving drunk and went to the ER. His medical bills were $25k, and the cost of the lawyer for his DUI was $3k. MIL paid his $2k health insurance deductible and the $3k retainer for the lawyer with BIL's DUI.
This does not include the car insurance she has paid for him since he turned 18 (the deal was that they paid for their own once they turned 18, which H did), nor all of the other money BIL has mooched off of her.
So H has told his mom that he will pay her back when she quits loaning money to BIL and finally teaches him a lesson on his actions, and when BIL starts paying her back. She never once has talked about this money H owes her, and has commented that if we tried to pay her back then she would just spend it on the baby by buying us things we need for it off our registry. However, BIL throws it out constantly that H owes their mom money from 5 years ago.
Should I pursue this further? Tell MIL that H came up with the amount of $1,200 that he owes her, and give her the money and say his debt is done? Or should I leave it be and let H hold his ground with his mom about the money?
We know that MIL is never going to stop giving BIL money, but it's just difficult when it has easily been $20k over the past 7 years she's loaned him and then here we are trying to dig out of debt and make smart choices without any help. While she's enabling him and paying for his lawyer to try and get out of the DUI that he deserved (which he lost the case anyways so it was money wasted).
TTC since 1/13 DX:PCOS 5/13 (long, anovulatory cycles)
Clomid 50mg 9/13 = BFP! EDD 6/7/14 M/C 5w6d Found 11/4/13
1/14 PCOS / Gluten Free Diet to hopefully regulate my system.
Chemical Pregnancy 03/14
Surprise BFP 6/14, Beta #1: 126 Beta #2: 340 Stick baby, stick! EDD 2/17/15
Riley Elaine born 2/16/15
TTC 2.0 6/15
Chemical Pregnancy 9/15
Chemical Pregnancy 6/16
BFP 9/16 EDD 6/3/17
Beta #1: 145 Beta #2: 376 Beta #3: 2,225 Beta #4: 4,548
www.5yearstonever.blogspot.com

Re: To pay back, or not to pay back?
I think the BIL was a turd for bringing it up, and I think that what is going on between BIL and MIL is their business and should have no bearing on your DH and MIL's loan.
The peace of mind would be worth the $1,200-$1,600 to me.
TTC since 1/13 DX:PCOS 5/13 (long, anovulatory cycles)

Clomid 50mg 9/13 = BFP! EDD 6/7/14 M/C 5w6d Found 11/4/13
1/14 PCOS / Gluten Free Diet to hopefully regulate my system.
Chemical Pregnancy 03/14
Surprise BFP 6/14, Beta #1: 126 Beta #2: 340 Stick baby, stick! EDD 2/17/15
Riley Elaine born 2/16/15
TTC 2.0 6/15
Chemical Pregnancy 9/15
Chemical Pregnancy 6/16
BFP 9/16 EDD 6/3/17
Beta #1: 145 Beta #2: 376 Beta #3: 2,225 Beta #4: 4,548
www.5yearstonever.blogspot.com
This. I would pay it back just to be free and clear of this "debt". Then you can show your BIL what it really means to be responsible

But the 529 sounds like a good idea.
I think the issues with BIL are unrelated to the debt H owes his mom. What your MIL decides to do with her money is her call. You should pay the debt back. That being said, it will feel good that no one can hold over your head that debt wasn't paid back to MIL. Plus once you don't owe her the money, you can start telling BIL, we made good by mom, when are you going to stop being dependent so much on her.
I"m with other posters and if MIL insists on not accepting the money, invest the money for the baby and when it's time, you can tell them Grandma make the starting contribution to this fund for you. It will mean something to your baby when the time comes that they need the money.
TTC since 1/13 DX:PCOS 5/13 (long, anovulatory cycles)

Clomid 50mg 9/13 = BFP! EDD 6/7/14 M/C 5w6d Found 11/4/13
1/14 PCOS / Gluten Free Diet to hopefully regulate my system.
Chemical Pregnancy 03/14
Surprise BFP 6/14, Beta #1: 126 Beta #2: 340 Stick baby, stick! EDD 2/17/15
Riley Elaine born 2/16/15
TTC 2.0 6/15
Chemical Pregnancy 9/15
Chemical Pregnancy 6/16
BFP 9/16 EDD 6/3/17
Beta #1: 145 Beta #2: 376 Beta #3: 2,225 Beta #4: 4,548
www.5yearstonever.blogspot.com
I couldn't owe money like that. I have never borrowed from family and I hope we never have to. I felt guilty enough owing ginormus companies money for H's SL debt.
Love: March 2010 Marriage: July 2013 Debt Free: October 2014 TTC: May 2015
It was a wonderful gift, but I borrowed that money throughout college so I didn't have to borrow as much in student loans and had planned from the start that I would only borrow what I truly needed and we would both keep track and they would get paid back.
TTC since 1/13 DX:PCOS 5/13 (long, anovulatory cycles)

Clomid 50mg 9/13 = BFP! EDD 6/7/14 M/C 5w6d Found 11/4/13
1/14 PCOS / Gluten Free Diet to hopefully regulate my system.
Chemical Pregnancy 03/14
Surprise BFP 6/14, Beta #1: 126 Beta #2: 340 Stick baby, stick! EDD 2/17/15
Riley Elaine born 2/16/15
TTC 2.0 6/15
Chemical Pregnancy 9/15
Chemical Pregnancy 6/16
BFP 9/16 EDD 6/3/17
Beta #1: 145 Beta #2: 376 Beta #3: 2,225 Beta #4: 4,548
www.5yearstonever.blogspot.com
TTC since 1/13 DX:PCOS 5/13 (long, anovulatory cycles)

Clomid 50mg 9/13 = BFP! EDD 6/7/14 M/C 5w6d Found 11/4/13
1/14 PCOS / Gluten Free Diet to hopefully regulate my system.
Chemical Pregnancy 03/14
Surprise BFP 6/14, Beta #1: 126 Beta #2: 340 Stick baby, stick! EDD 2/17/15
Riley Elaine born 2/16/15
TTC 2.0 6/15
Chemical Pregnancy 9/15
Chemical Pregnancy 6/16
BFP 9/16 EDD 6/3/17
Beta #1: 145 Beta #2: 376 Beta #3: 2,225 Beta #4: 4,548
www.5yearstonever.blogspot.com