Finding insurance and getting off SS? HALP!

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Okay,I'm thinking about doing Live Ops(a virtual call center) as a job.
Problem is, If I get a job,I have to tell Social Security, and then I don't think I'd be eligible for Medicare anymore...
Does anyone here pay for their own insurance(Not a benefit from their employer, but because they are self-employed they don't have it automatically...) and how much do you pay?What's covered?
Another thing about Live ops:you don't start making full money right away, since you don't get that many calls at first.You also have to do your own taxes quarterly I believe.

TL;DR: Anyone here self-employed that had to notify Social Security and find their own insurance? HALP.

I cannot see what state you are in but I can say this, odds are you will not be able to purchase insurance on the open market if you are dx'd with an ASD and receiving treatment for it in some manner. Your state may offer a risk-pool like set up for those who cannot get insurance but not all states do so and the cost is a little higher.

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This is the biggest issue I have with our current health insurance system. First, it is an all or nothing type set up where either you have to be covered for everything large and small, or your get nothing (you cannot even self-insure for one thing). The 2nd is that the insurance company is free to state that they will not cover a pre-existing condition for a period of time but yet can also exclude based on that condition. If they are going to exclude it, then they should not have to cover you for it. Finally, this is the biggest single reason why social services rolls are so high. I would bet more people would work if they did not have to worry about losing their healthcare insurance.
</soapbox>

I'm in Indiana.:/ is there a website anywhere that lists something like this?