Each person can give $13,000 gift tax free annually to an individual for federal tax purposes. It looks like there is no gift or inheritance tax in WI after 1991 but I am not a WI lawyer.
I cannot answer part 2 because I am not sure of the type of insurance is referred to. If it is unemployment insurance I don't think it is a problem.
Check with a WI lawyer first.
Disclaimer of California Attorney. Laws differ form state to state. Although the above response is believed to be accurate, it should not be relied upon as any type of legal advice because the information provided is incomplete. It is intended to educate the reader and a more definite answer should be based on a consultation with a lawyer. No attorney client relation is formed with me without a written contract.
Good Luck starts with a strategy and a plan.
Robert J. Suhajda, MS,CPA
17721 Norwalk Blvd. #43
Artesia, CA 90701
Tax Relief Lawyer. Former financial auditor and controller. Admitted to US Tax Court, Income Tax, IRS representation, Fiduciary income tax returns, Estate and Gift tax returns, Homeowner Association Strategist.
If your reference to state insurance means medicaid, that is a huge problem. Call the Wisconsin State Bar association at 800-362-9082 and ask to be referred to an attorney who specializes in medicaid before cashing out the CD. Cashing out the CD can make your parent ineligible for medicaid.