Don’t know where to begin

Here is my situation- any guidance or recommendations would be welcome.

I’m a 25 y/o male still under my dad’s insurance because it’s great and I have been avoiding having to switch. Unfortunately I’m turning 26 next month and starting to stress about getting coverage. I have no health conditions and have not visited the doctor in years (other than annual checkups- no issues yet)

Anyway- my partner is graduating this month and we will be relocating to a new state. I’ve spent the past 3.5 years as a case manager for unhoused individuals and am very burnt out. After she graduates I am planning to quit my job so that we can both recover mentally from a stressful few years. Nothing crazy, just ideally Jan-April to travel/visit friends/take a break from the social work grind. I found a contract side-hustle that brings in around $2000 a month but comes w no benefits. It’s fully remote and would be ideal for my dream scenario, however I need insurance.

My hangups are- I have residency in the state that I am about to move out from (Michigan) but planning to travel around and stay with friends and family for the next three months. I won’t have an active lease and am not planning to return to live here in the future. Should I use the state that my parents live (Tennessee) as my residence if I work remotely and am not on a lease?

I’d be willing to pay $300-400 a month for short term coverage for Feb-April but I am unsure where to begin w this process.

I’m salaried at 45k with my main job but also was working part time as a bartender most of 2023 so I’m unsure how eligibility works in this stance. I also am unsure if it would work since I will be leaving the state so soon.