My husband was/is working at a job where he pays $123. a week for coverage out of his paycheck, supposedly the company pays the other half of that coverage (2 adults, 2 under 18's). It's PPO with a $1000 deductible and then 80/50 (25 office visit 50 emergency room).

He just got a form from his current employer that says that if we want to continue coverage for July we only have to pay the $490 that we'd normally pay and then in August pay $1000 for coverage per month after that.
Anyway, he's moving to a new job, and we called the insurance company to see about continuing coverage with them. They just gave me a quote of $530 a month which is a little bit more than what he's paying a month, and something doesn't feel right here. (this will relate to question 1) First of all, it's not continuing coverage per se, we do have to reapply for the coverage, which means that I suppose they will change the quote, due to a minor health problem I have.
Question 1. Does something about this situation sound fishy? If we are paying $490 a month from his boss, and will be paying $530 a month if we go it ourselves - where does his boss get the $1000 figure? (all figures are estimated. It seems to me, that his boss is just "telling" his employees that he's paying for 1/2 of the coverage, when really they aren't.
Question 2: Did I not ask the insurance company the right question perhaps about coverage. I asked to continue coverage, and they said that we couldn't do that, but we could reapply for coverage with an application, but they didn't say that they would re-evaluate our coverage costs. My husband says not to trust this original quote, and frankly I'm new to all of this insurance stuff and have no clue what to do now.
Question 3: We are both diabetic, and he has slightly elevated blood pressure, I am insulin dependent and he isn't. I have a minor blood disorder (Polycythemia Vera) that requires blood work and phlebotomies once in awhile - I'm overweight and take medications for depression. Does stuff like this figure deeply into being accepted for coverages?
If you can dumb down your answers for a confused woman - it would be appreciated.
I'm in Illinois, if that helps at all.