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this link is probably what youre looking for:
sthief thread
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sthief's situation and this guy's are worlds appart. This guy has a house, and a young baby.. and a gap on his resume may look odd.
OP, I think one of the biggest things you need to worry about is health insurance. If you haven't had to obtain it at your and your wife's age, it can be an eye opener.
I worked for a dotcom in the late 90s that eventually shut down. When everyone was laid off, we were offered Cobra from the state (or is it federal?).. in any case, since the company was completely out of business, they were only required to provide 2 months of cobra benefits... meaning that I had to go obtain private insurance.
Now.. I'm in a similar situation as you, similar age, young kid, 6 figure salary, lots of savings, bla bla bla.. I was willing to pay big for private insurance for me and my family... guess what.. we were *denied* Even if we only wanted catastophy insurance for $1K a month... *denied*. I should also point out that we didn't find out that we were going to be denied until just before our state mandated insurance was going to lapse. The insurance companies we were working with and getting quotes never indicated that there would be any issue. So, we picked the one that made the most sense financially and submitted our application only to have it denied about 3 weeks later.
Now, I managed to get another job before the cobra benefits lapsed so I didn't continue to pursue it.. but you really, really need to research your insurance options before you drop your employer's insurance.
If I ever go pro.. and I'm considering it some day.. I'm going to figure out a way to start a small (shell?) consulting company or something and use that to leverage a group plan for small busineses if I can't manage to get private insurance again.
Oh.. and even with those 2 months of cobra (which I think I had to pay over $2K for) my medical bills were huge when I did need to go in. My wife had post pregnancy complications, my son initially had some issues, and I slipped on the stairs and broke 2 disks in my back and had to go to the hospital. (I'm fine now, luckily)... anyway.. with all of that, even with cobra, I still had to pay around $12K for medical and ambulance bills because hospitalization wasn't fully covered and the max out of pocket cost for deductables was calculated per-person.
slightly off topic:
Until I had to deal with private health care, I had no idea how f'uped our health care system was. If I wasn't well off, I would have been screwed. I could very well see how the high insurance cost (and soon to have been no insurance) plus medical bills could tap a less afluant family of all they own.
Anyway.. the lesson here is to make sure you have a plan for insurance and that you will actually be able to get it.