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insurance suggestions?

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insurance suggestions?

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My job's ending. My last day (for real this time, no more extensions) is December 2. Since I'm working in December, I'll have coverage for December, but then it ends.

I don't have a job lined up in Chicago. I feel fairly good about my odds of finding one once I get there - you gotta be local both for the beating feet part and for using temp agencies (you have to be present in order to jump on short notice opportunities) - but even after I hire on I will have to wait probably 90 days for a probationary period before insurance coverage will start. While I have found that using a temp agency really makes finding a job easier, it also extends that wait time, because when you're with the agency, you are the agency's employee, and the company you're working with is the agency's client. Mostly I have found that even if a temp agency provides insurance, it's not worth partaking.

So. Even in a pretty good scenario, I might be without corporate coverage of my insurance for up to four months. In previous years, I have just let my coverage lapse after my job ended and picked it up when I became eligible at the new place. With my relatively new diagnosis of diabetes, though, I'm not in the same boat as I was the last time I changed jobs. My meds aren't a problem - my nurse practitioner prescribed me six months worth of them so that I could buy them all now while the discounts that go with my current coverage still apply. My main worry is overall cost: if I let my coverage lapse now, I'll have a preexisting condition, which I am told will mean that the underwriters can slap riders on any new policy for me that will for up to two years. As I understand it, riders are baaaaad.

The way to avoid this is to pay for Cobra coverage between jobs... but that will cost me $458 a month, which will come to almost $2000 for my hypothetical four months. That's not even considering the possibility that I WON'T find a job. I'm competent but there are a lot of bodies out there right now, so I have to be realistic about that possibility.

I don't know if there are other options for insurance coverage that also count as "not lapsing in coverage," I don't know how much more the riders will make coverage for me and whatever company hires me once I do get insurance again, and I don't really know how to find out these things. Yeah, "Google it," I know, but in this case, I don't really know what I'm looking for, and there's a plethora of information out there; based on some preliminary searching I assume much of it is scammy crap, and in this case I am ignorant enough that I'm afraid I will fail to sort out the chaff. Any research abilities I have are overbalanced by the fact that insurance and the issues that surround it make me feel stupid and I tend to blank out, and the last thing I need right now is to also get screwed in a really stupid and avoidable way.

So that's my sad story. If anybody has advice, I am exceedingly interested in hearing what that might be.
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