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So it’s a couple of different situations, sounds like:
mom loaned someone $ more than 5 years ago. That person is actually paying mom $ each mo. That $ will most likely be looked at by Medicaid as “income” paid to her, when they review last 5 years of bank statements. If she doesn’t spend it all that month, it then rolls over to become an asset. Medicaid has both income & asset limits. If monthly loan payment takes her over income limit, Medicaid will likely see her as over the income limit so not eligible. You imo kinda need to have some specific of documentation drawn up that clearly shows its a loan and is time limited. So like it ends say 2/3/2020 and not a continuous income like SS $ is. Comprende? Could you DIY this, maybe but loans or memos of understanding or Promissory Notes have had to be done just right to be enforceable.

The second $ issue, that’s way way WAY convoluted. Is this bordering on elder fraud, coercion, kinda stuff. It reads that way. This level of stuff imo needs an atty to look at. There’s just too much $ and liability for the “good” family member to be on the hook for IF Medicaid rules her application ineligible. Gather up all paperwork, Take some of mom’s $ and see a NAELA or CELA level of elder law attorney.

To me its just just too many moving interlocking parts for a DIY.
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igloo572 Sep 25, 2019
My bad, missed the conservator aspect.... all this now is in their wheelhouse. I do think regarding the $ currently being repaid, if it’s actually in repayment and the borrowers have been doing this as regular set amount & routinely for a several months, it probably can be viewed as an existing & established verbal agreement.
But id be concerned that unless the full amount loaned is repaid, the difference might be considered “gifting” and will place a gifting transfer penalty. All this is just sticky to deal with and before you even get into the new checking account & its $ move to a mystery account.
BUT
since a conservator was named, that’s pretty significant action. Conservator is family or outside person appointed by court? whatever the case, it’s the conservator who needs to be in charge on all this. It’s not you meeting with an atty.
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If your asking about penalties, I’m guessing there was a transfer of property or $ or other asset that happened.

So what was it?
Ballpark figure what realistically was value?
Is person(s) you gave to at all likely to transfer property back to you, or give the exact amount of $ back?
When did this happen? Like month date year for last $ move?
When would you likely / realistically need to be living in & apply for LTC Medicaid?

Transfer penalty is a math problem. Division (fraction).
Your state will have a daily LTC Medicaid NH reimbursement room & board day rate. Average is abt $175 a day. That # is denominator. The amount given is numerator. There can be other things that factor in, but basically it’s a simple math problem.
So say you transferred Sonny your fully paid for home with tax assessor value of $234,567.89 Dec. 25, 2016. That’s the numerator (top).
Your state pays the NH $198.76 a day. That’s the denominator (bottom)
1,180.15 (quotient). That’s penalty by days of ineligibility.
Not by amount of $ but by days ineligible & disqualified.
So basically for 1,180 days you will be disqualified for LTC NH Medicaid even though you could be now impoverished with say $1200 in savings and so under the 2k non-exempt assets “at need” financial eligibility max and you are totally medically determined to be “at need” for skilled nursing care and you are living in a NH.

IF you apply before January, 2023, the transfer will be an issue as most states have a 5 year look back. Date of penalty starts day 1 that you applied for Medicaid.

To me, I don’t think penalty inquiries are a DIY unless it’s a lower value amount and kinda close to the 5 year mark. Like an old car.
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anonymous957160 Sep 24, 2019
Long story short She is in a skilled nursing facility that excepts Medicaid we are in the spend down process, she is widowed , There was a loan given outside to look back. The payment will be made within the look back . And will be spent down before we apply for Medicaid. The payment of the loan is a lot less than the original amount of the loan. There was also a new joint checking account created by a family member that transferred Moms money into this account. The spending was not typical for the mom. The spending was not typical for the Mom there was transfers from the joint checking account to a Nother account that we are not sure who it belongs to. This joint checking account has been closed the day we received a conservator The joint account would be open and closed in the five year look back. 
We are located in Colorado We are trying to see if either of these two items of the joint checking account and the loan will cause any penalty when we apply for Medicaid
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We need more information to advise. Did you apply for someone and did they deny and assess a penalty? Or are you afraid of a penalty? If so, why? In some cases that fear is warranted, in others not as much. Does a loved one need care and doesn't have the funds/insurance to cover it? If so there are ways to get that. Give more info so we could help more.
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anonymous957160 Sep 24, 2019
Long story short She is in a skilled nursing facility that excepts Medicaid we are in the spend down process, she is widowed , she had dementia. There was a loan given outside to look back. The payment will be made within the look back . And will be spent down before we apply for Medicaid. The payment of the loan is a lot less than the original amount of the loan. There was also a new joint checking account created by a family member(same family member as the loan) that transferred Moms money into. The spending was not typical for the Mom there was transfers from the joint checking account to a Nother account that we are not sure who it belongs to. This joint checking account has been closed the day we received a conservator The joint account would be open and closed in the five year look back. 
We are located in Colorado We are trying to see if either of these two items of the joint checking account and the loan will cause any penalty when we apply for Medicaid.
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JoAnn gives you good information, but the qualifications are VERY different if there is a spouse involved, one who will continue to live in the family home.
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JoAnn29 Sep 20, 2019
Forgot to add the Community spouse.
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Medicaid can be daunting. Each situation is different. Each state a little different in the rules. Basically though it comes down to the persons income. Everything has to be liquidated. Bonds, shares, IRAs, CDs and some insurance policies. There is a spend down process where all the persons assets have to be used before Medicaid will take over. The recipient will be allowed to keep a house and car but...none of their money can be used to up keep either. Penalties come in when in the 5 year look back the person has given away or gifted a large some of money. Lets say they sold their house and gave ea one of their 3 children 10k each. If Medicaid is needed within 5 years, that money will need to be given back or someone will need to pay for Moms care until that 30k is made up.

I am just giving you the basics here. Your best bet is to talk to a caseworker at Medicaid. I wouldn't consider a lawyer unless you run into problems. I would then get a lawyer who knows Medicaid.
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A little more information will get you better answers.

Is your mother in a nursing home? Is she currently a private pay patient? How long will her funds last?

Has she gifted/given away significant amounts of money/property in the last 5 years?

What state does she live in?
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anonymous957160 Sep 24, 2019
Long story short She is in a skilled nursing facility that excepts Medicaid we are in the spend down process, she is widowed , There was a loan given outside to look back. The payment will be made within the look back . And will be spent down before we apply for Medicaid. The payment of the loan is a lot less than the original amount of the loan. There was also a new joint checking account created by a family member that transferred Moms money into this account. The spending was not typical for the mom. The spending was not typical for the Mom there was transfers from the joint checking account to a Nother account that we are not sure who it belongs to. This joint checking account has been closed the day we received a conservator The joint account would be open and closed in the five year look back.
We are located in Colorado We are trying to see if either of these two items of the joint checking account and the loan will cause any penalty when we apply for Medicaid
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