Hi Jody,
I work for a health insurance company and I am getting banded on June 28th (here in Kentucky). I would be happy to try and answer your questions.
To tackle Question 1: Your new insurance company may not hold you accountable for pre-existing unless they have a pre-existing clause on their policy. To get the pre-existing clause waived (meaning it won't apply to you), you would have to have had continuous coverage for a consecutive 12 months prior to your NEW coverage with no bigger than a 63-day gap between the two policies. WITH THAT SAID, it is VERY important that you look into the health benefits of the job that you are considering because most insurance policies DO NOT cover bariatric surgery. I deal with thousands of policies and only about 10-15% of them actually cover the procedure. As far as how long you need the fills, I don't know the answer for sure, but I think its a safe bet its based on each individual and how much s/he has to lose.
Question 2: A lot of insurance companies (including the big ones like Humana, Anthem, BCBS, Aetna, and United) all offer individual policies. The drawback? They are no where NEAR as good as commercial group policies you would obtain through your job and I am almost 100% sure they would not cover bariatric surgery or any office visit/testing/fills that may be involved (I don't thnk they even cover maternity, which is mandated to be covered by all commercial fully-insured groups). The reason a lot of people have these policies (and cobra for that matter, which is basically an extension of your current policy, only instead of your employer paying most of your premium, you end up with the entire cost) is to close the gap between switching jobs so that they do not become subject to pre-existing again (remember, if a company applies pre-existing to their policy, you WILL be subject to it if you cannot provide proof that you were covered for a consecutive 12 months with no bigger than a two-month/63-day gap between the old and new policies). Another concern I have with switching jobs is that if you opt to have the gastric bypass and then switch jobs, AND your new policy DOES NOT cover bariatric surgery, they will NOT cover any complications that you may have with that surgery. So with a higher risk surgery, the more you are at risk you are for high medical bills.
Question 3: I have never heard of anyone being denied health coverage because they had gastric bypass. I have however heard of life insurance and other types of insurance policies denying coverage or slapping you with a higher premium because with a procedure like that, no one really knows what the complications could be and therefore view them as high risk. But for regular health care coverage, I cannot see any of the big ones doing that, especially if the policy does NOT have a pre-existing clause on it. But, nothing amazes me with insurance these days. Working for them is certainly NOT my proudest admission, however it has made me very knowledgeable in the subject. I wish your friend the best of luck with her situation and hope I have sufficiently answered your questions.