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His case is pretty cut and dry, I’m wondering if I can do it myself.

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You don't need to pay anyone to do that. The friend qualifies on both the income and resources limits?
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He needs to go to your local Social Services in your county and apply. They will need proof of income and statements of bank accts. and proof of CDs, IRAs etc.

This is just for health insurance. Medicaid for LTC is a little different if he is not able to apply himself.
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