Realize that you are not "put on Medicaid". Medicaid is an "at need" entitlement that you have to apply to and be eligible for both medically & financially. Medicaid is quite different than Medicare or SS - which are entitlements that you have actively participated in by $ paid into FICA.
5 year look back basically means having everything done before the end of this year and not ever needing to apply for Medicaid before January 2022.
Medicaid rules are different for each state. You would need to find a lawyer who specialized in Medicaid and elder law for the state of Connecticut. Please realize that anything you try to set up now will still be subject to Medicaid Recovery after you die if you are over 55 or be assessed a transfer penalty before you receive services unless you don't require services until 5 years after the date that you "take action to protect your home and other assets". Medicaid expects that you will use your assets for your own care (rather than protect them for the benefit of friends and family after your death) before you apply for benefits intended to help low-income/poverty level individuals. If you have a family member as an in-home caregiver, you may be able to have them apply for exemptions on the house from Medicaid Recovery if they provide care to you that keeps you out of long-term care for at least 2 years. The lawyer can also tell you whether any actions taken prior to now will be subject to a 5 year look-back or transfer penalty. Medicaid is also limited by your monthly income (pensions, Social Security, etc) so a lawyer is your best resource for how it works in your state.
5 year look back basically means having everything done before the end of this year and not ever needing to apply for Medicaid before January 2022.