Should I Continue Medicaid Coverage or get an ObamaCare plan?

I am a 53 yr-old teacher, unemployed, with MANY declining health needs. I’ve been searching and feel that despite my experience, I will be passed over for hiring due to health needs (various frequent appointments and quite a list of required prescriptions I take).

I’m thinking that the fastest way to get back to some sort of feasible work is to begin just substituting, there’s plenty of work there and still allows me to keep appointments.

Will Medicaid “cut me off” as I begin to earn more than just what I currently receive on unemployment?

I probably would qualify for disability, but still want to remain working (AND teaching, which I love) as long as I can…..and then…..I would be thrown into finding a health care plan and be out of the open enrollment timeline as well as have MANY pre-existing conditions + just plain not know where to start….HELP AND ADVICE are welcome and sought at this time.