I just quit my job, and signed up for a $7000 deductible plan coupled with an HSA. Maximum annual-out-of-pocket of around $10,000. If you are working, your employer needs to sponsor the HDHP and HSA for you to have access to it I think. My previous employer didn't.
COBRA for me and my boy would have been $1150 a month. Moving him to my wife's plan would have been $300/mo.
Both of us on the HDHP costs $214/mo through Regence. I figure I'll squirrel away $200/mo through HSA Bank (which I haven't heard good things about. Too many fees if you aren't careful), and then open up a TD Ameritrade account through them that allows for investing in anything under the sun (other than options or on margin). Essentially a second IRA, but you have to spend it on healthcare. The reason I am going HSABank is because that appears to be the only way to get a full-service brokerage account. Someone let me know if they know of other options that allow this.
My main concern is ER visits, but given that we are going to be saving about $10,000/yr going this route (about the same as the maximum out-of-pocket), I'll takes my chances.