What paperwork will I need to save for five-year lookback?

Any documents/bills that reflect payments from home repairs or emergency fixes! For example, if a pipe burst and it cost 4K to fix/repair proof of any homeowners insurance payments should be kept. This proves the money was not gifted. (I HAD TO come up with these papers/cancelled checks followed up with bank statements/receipts to show the chain of claims/payment funds when my spouse applied for Medicaid. I had to show there was a homeowners policy in place. Medicaid even asked me to present a picture! So I called my friend who had a good enough camera to photograph under the sink to show the replacement part that still had it's tag attached!!

Anything that required payment of any amount that has to do with medical or Property issues may be requested at any time.

One means of tracking medical expenses is to get a copy of prescriptions filled at the pharmacy. The local utility will print out running statements of monthly billings for a period of time. If there are any prescription containers, those will have the doctors name/phone number. Your must present your proof as the person in charge of affairs.

I experienced documentation requests for my spouse, living plus Mom after she died. Much happened in the same time frame.

In conducting business for Mom's estate from 2K miles away, I mostly ran into identity issues. Proving I was the legitimate person-very hard with some entities. I had to mail/fax my ID & paperwork to establish mother-daughter relationship, proof I was the designated person etc.
A couple times I was at the teller's window with a paper check in hand, and an employee telling me I could not deposit the check! I was merely trying to transfer her West Coast bank account to a bank in the South. It was the same bank, only a different location.

In all health and financial matters I have had to prove to each provider or institution my legitimacy. I was held to a higher standard of proof as I was 2K miles away. This has applied with creditors, medical, banks, Social Security and others. As long as you have no criminal history or bad credit history it eventually pulls together. I was background checked with several institutions.

If your relative has a state issued ID or a drivers license make sure that ends up in your possession. Health insurance cards must be copied and kept in your possession when the time comes. You will be asked to present them at times. Get copies of all her health insurance cards, auto insurance, homeowners etc! Do so without delay!

You may very well end up having to hire an attorney to help resolve some situations. So I got busy and talked to people in Mom's area and went online to research attorney practices within that community. I eventually made it through this process right alongside getting my husband's Medicaid case established. If you do the legwork now, it will help if you have to ever obtain guardianship or executor status as well.

Mail/bills/correspondence will reach you if your relative will list you as a person authorized to receive copies of bills. If not already done, you should try to convince your relative to sign forms with providers allowing you to conduct business too. You may have to consult an attorney about this if you live so far and can't be present to handle these details while your relative is living.

Contact some of her known friends and neighbors. They may be willing and able to convey information to you that helps determine what direction you need to go.

Proof of you as the legitimate person can require your identification multiple times. If you are going to handle affairs after death too, this will help accomplish such details. Sort of like doing 2 things at the same time.

Type up your own spreadsheet or similar document and just start typing in whatever bits of info you obtain - account numbers, medicines, personal phone numbers, names/addresses/phone numbers of places you need to deal with.

To be on the safe side, save everything that is related to your relative. Everything. And organize them by categories: meds (prescription drugs, OTC meds), dental (cleaning, toothbrush, toothpaste), clothing, food (meals in wheels, groceries), etc... It takes a lot of effort but will save you a lot of headache later when it is time to apply for Medicaid. Let Medicaid decide what they can accept or not.

Also - Medicaid will want a copy of any check written for $500 or more.

Hi...
I just want to Add. Don't be nervous about this 5yr look back.
I am right in the middle of this ..

I would suggest getting mailed copies of bank statements. Not online only.

Yes, Save anything regarding real estate, med insurance, bank, & here's my 2 cents...
By all means, CALL MEDICAID/STATE OFFICE & simply ask...😁 im very surprised how helpful they are & I ask social workers anything because i'm always being honest & have nothing to hide..
Goodluck

Many good answers...However, hire a "well-recommended" elder care lawyer.
I can't say enough about "well-recommended." I interviewed a couple of them who did not know their rear end from third base...

Grace + Peace,
Bob

The most critical thing I encountered when getting my Mom qualified for Medicaid, and sorting through everything with an Elder Care Attorney, was the cash/ checks that my father had periodically given me to help with my insurance (medical and car) and assisting with my daughter's apartment rent for just a few months before she graduated.

I had a bad divorce and lost everything, and moved in with my parents to care of them as my Mom had progressive dementia, my Dad COPD and stage III CHF. I am an RN, but due to the issues with both, constant doctors appointments, and frequent hospitalizations, I was unable to work a "regular" job. Retrospectively, had I had appropriate counsel, I would have set up a caregiver agreement. Because I did not, every single check that Dad provided to me I had to account for.....and I was required to pay back every cent before Mom could become Medicaid eligible. This was several thousand dollars (just a few hundred a month for 2.5 years), but it was within the 5 year look back. It didn't matter that I was taking care of them full time....I didn't have a "paid agreement". Medicaid looked at it as if it were cash gifts for heavens knows what....but it was only car insurance, rent for daughter, medication and medical insurance. Not even a new pair of shoes or a haircut.

So it would be a good idea to inventory the bank accounts to see if "cash" or "check gifts" were provided to anyone....this could be a surprise if you all of a sudden are applying for Medicaid, and there is a penalty period due to needing to repay the "gifts".

It would not hurt to go through the exercise of gathering the 5 years of documents with an Elder Care Attorney sooner rather than later. Better to be prepared in case you need extra spend down or need help with a situation as I described above. My Mom entered Memory Care....and was there for 3.5 years before she was literally kicked out to a nursing home due to increased care requirements. She was on hospice 3 times during that period...and not expected to make it....but she did. By the time we moved her to a Nursing Home, we'd paid over $350,000 to the Memory Care facility. So we had to apply for Medicaid because I was about to exhaust their savings.....and I am taking care of my almost 93yo Dad at home, monitoring him 24/7. I need to protect assets in case he one day needs care beyond what I am providing.

All receipts only if you are Guardian.

1) Online payment systems ask for personal details, not POA's often. One of the first things I did was set up her accounts at her credit card companies to make payments.

2) This is the list an Illinois SNF gave me for medicaid application. Sent 85 PDFs and had a family friend get a copy of her 31 year-old divorce decree.

Your state may differ, but this is a headstart:

* Driver's license and/or photo identification card
* Birth certificate or Baptismal certificate, Immigration papers (if applicable) 
* Social Security and Medicare Cards
* Marriage certificate, Divorce Decree, Death certificate of spouse (if applicable) * Legal Guardian / Power of Attorney papers
* Complete health insurance cards and verification of premium payments for patient and spouse (if applicable)
* Monthly bank records to application date, 60 months of checking account statements,  60 months of saving account statements, credit union, money market, IRA, mutual funds, etc…
* Explanation of deposits, withdrawals, and copies of checks over $500 excluding Social Security or Pension income, over the past 60 months.  
* Stock and Bonds owned or sold in the last 60 months
* Social Security, Pension, Railroad Retirement, Disability and/or all income checks.
* Federal or State income tax returns for the past five years. 
* Deeds, property tax statements, mortgage contract, contract for deed, sales contracts, on any  real estate owned currently or sold in the last five years.  Title and registration on any/all motor vehicles. Payment book if applicable. 
* Complete life insurance policies. Obtain letter from insurance company (on company stationery) showing cash and face value. 
* Unpaid medical bills for 3 month period prior to date of application. 
* Burial plot deed and burial plan contract, proof of ownership, and value.

A check for the exact amount was issued to me and spouse to cover our homeowner damage claim. I deposited it into our joint checking as the check was issued to both of us. I immediately wrote a check for the exact amount to the contractor who repaired the damages. It was fully deducted from our checking real quick.

That said, I had to provide papers, copies of checks to show it was a straight insurance transaction. If your elderly relative may have had any home repairs - during this look back period - try locating that information. If she lived in a house before moving to her apartment, it's possible she could have made unusual deposits/withdrawals that will be reflected in her bank statements.

You also need deeds to her house, marriage license, repairs on her house, donations, bank accounts, wills, prepaid funeral, car ownership, it's a long list....
They should have a list of items you need.....ask for it...