I've always been worried that once you stray from the protections offered in a group plan, the insurance will just dump you if you have any major issues. And then once you're dumped it's a "pre-existing condition" and now no one will cover it but a group plan - forcing you to join a company again.
There are other options, but they work differently and seem scary to most people who are used to letting the company deal with it at a first glance.
Source: I was a health insurance salesman for a short period of time, and was licensed to sell for most of the insurance companies out there. It's part of why I'm not scared of going out on my own and freelancing -- I know enough about how insurance works not to worry about it, and can even sell myself a policy and get commission. However, it's been a couple of years, and I probably can't give you accurate, detailed information -- many of the insurance companies are revamping their business models and policies in anticipation of Obamacare.
At least here in Virginia (I'm no insurance expert), a group is 2 or more people. My wife is officially a shareholder of my company, and so she and I have a group policy. We pay a little under $1000/mo to insure the two of us and our two girls.
I guess I could just ask an agent. I'm in IL, and a group minimum is also 2.
It did mean, though, that I have my own policy and my kids are under my wife's policy. So if my wife and kids go to the doctor a bunch and pay their deductible, should I need to go I'll have my own deductible to pay.
The small company I work for offers group insurance, but we all have to pay full price - they don't subsidize any of it.
They do take it out of our paychecks pre-tax so we don't have to pay taxes on it - but it would be tax deductible anyways at the end of the year.
My last employer was paying about $1.7K per month for a family of three. Costlier than usual because it was a very good plan. I could not find a with similar levels of coverage and deductibles for cheaper outside.
The key thing that varies between plans (I am based in California) include deductible and coinsurance, which can be traded off with monthly premiums. Lower the former two, the higher the premium.
I pulled out my families older insurance claims data when my employer was paying to estimate my future expenses for each family member. Based on that, I considered various plans and ended up choosing a plan with higher deductibles but lower monthly premium (~$600 for the family). Mostly likely, this will save me a lot over the low deductible plans. This is true even when I expect to be paying just about as much in deductibles/coinsurance per month on an average based on the past data. If things go wrong, I may end up paying a lot more, but still capped by the out-of-pocket maximum that is not much higher than $1.7K per month.