I’m costing out a 1 year hiatus from work, one of the concerns is
benefits cost as I currently receive from a cushy corporate job:
– Health (Doctors & Medicine prescriptions)
– Life, Accidental, Short & Long Term insurance
– Also interested in COBRA coverage & costing (if you’ve had to
recently depart the lazy M)

I’m looking at paying this out of my own pocket (as I’ll be on my own,
with a single income family).

Any suggestions on providers? agents? structuring it to reduce tax
(can I pay for it out of a Flexible Spending Account for example)?

I was in your exact same position about a year ago, wanting to leave
Microsoft, and trying to calculate the cost of my benefits.

The exact cost of the COBRA option is published on either hrweb or the
benefits website on the Microsoft intranet.  If I recall correctly, it was
coming to about $1250/month for my family of four (me, wife, two kids)
including medical and dental.  But that was for the specific health plan I
was on, and yours may be different.  Plus that was a year ago, and costs
have risen since then.  I decided COBRA was too expensive for our needs.

Since leaving Microsoft, I am paying for our own health insurance with
Regence Blue Shield.  Because we are a relatively healthy family, I opted
for the lowest premiums and highest deductibles.  As such, we are paying
$192/month for the whole family with a $15,000 deductible per person.  This
basically means that we pay all of our own medical bills unless there’s a
major catastrophe.  We no longer have dental insurance, and so are paying
our own dental bills which is basically just the regular cleanings and
checkups.

The main point of life insurance is to compensate for a lost income in case
of death.  Not to be morbid, but if you have no income after leaving MSFT,
then your death wouldn’t cause any financial hardship for your family.  So
you may just decide not to get life insurance at all.

I use Lifewise myself, but you should check out the Microsoft Alumni
Association’s health care plan.  I’ve heard its good from random
people on the street (or, at least random people at various tech
gatherings).  I can’t really speak to how good Lifewise is, since it’s
one of the high-deductible plans and I’ve never needed it for
something serious.  Insurance is annoying that way – there’s no real
way to stress test it before you actually need the thing.