relevant YC posts/articles:

https://qht.co/item?id=2247560

https://qht.co/item?id=2851224

links from the comments, or elsewhere:

https://be.freelancersunion.org/benefits/ (you probably want to look this up, since they provide discounted health insurance plans for people in and around NYC)

http://www.nase.org/Membership/OptionalBenefits.aspx (smaller benefits, not full covereage, for people across the US)

http://www.anthem.com (For people in California - a sufficiently high deductible introduces risk but can drop your deductible to around $150-200 or less; mine is $108)

If you have a pre-existing condition, then you might find a plan through your state: http://www.healthcare.gov/law/features/choices/pre-existing-... (is this an outcome of Obama's Affordable Care Act?)

deciding whether/how to claim this on taxes (I haven't quite fully understood this, though):

http://www.irs.gov/newsroom/article/0,,id=220839,00.html

http://www.irs.gov/newsroom/article/0,,id=223666,00.html

http://www.usatoday.com/money/perfi/columnist/block/2011-04-...

advice via Reuters, FWIW: http://blogs.reuters.com/small-business/2010/12/06/health-in...

For S-corp >2% shareholders have some pretty specific instructions. A health-care reimbursement gets reported on the W-2, but is not taxed.

See the last section on: http://www.irs.gov/newsroom/article/0,,id=200293,00.html

EDIT: While not an unbiased source, this article indicates that my assumption above is exactly right: http://reason.com/blog/2011/06/01/new-york-states-highly-reg...

I think, perhaps, the fact that NY has such comprehensive support at the low end of the income distribution, through medicaid, family health plus, healthy NY, etc., causes all of those young, healthy but lower-income people to drop out of the market for insurance. This leaves higher-income and older people in the self-insured and employer-sponsored pools, driving up the base rates.

In any event, a study by the Manhattan Institute, as referenced by the article, isn't very trustworthy. It would be very hard for them to release a study that said anything different, which to me means that there is inherent bias.

Options to consider * alumni associations, affinity groups, clubs etc. may offer health plans * talk with an insurance broker. Yes, a real live person, as they will be knowledgeable about the current market and any issues with specific carriers and plans. They usually are free to talk with and obtain quotes from.

If you can do it, get a high deductible insurance plan with an HSA for the years in which you are not having a baby. HSA contributions get some tax deduction status and those unspent HSA dollars can be carried in to the future. My CPA says HSA contusions are a good way to save for long term future medical expenses.

For the plan year you get pregnant, aim to understand the total costs and can an HSA / high deductible plan fit your finances. Will you be comfortable taking on the out of pocket expenses (the high deductible part) and continue making contributions to the HSA?

Will/can your wife work for a company that can offer health insurance?

Getting a plan in place is something that will take 2 to 6 weeks to get ini place so don't wait too long.

Now for the bigger question: do you have disability insurance and life insurance also in place?

Fyi, COBRA will most likely be more expensive than any plan you can get at the family level.

Hope this helps:)

> If you can do it, get a high deductible insurance plan with an HSA for the years in which you are not having a baby.

this seems like a good strategy. why not just use an HSA exclusively? is it due to risk of complications/cost during pregnancy? or do pregnancy costs likely come close or exceed premiums of a traditional plan anyhow?

> Fyi, COBRA will most likely be more expensive than any plan you can get at the family level.

why is that? my wife is looking to quit soon, and is coming from a fairly large organization. and it seems like the cobra, group-negotiated rates are slightly better than the family rates i'm trying to negotiate on my own. just my own experience.

Having a baby has some uncertainty; is the baby growing fine, is the mother doing well, how will the birth go, what about the first year, etc. That is why I suggest looking at the total costs, the mother's health, and what financially you are willing to take on up front with an HSA. Sorry I do not have a clear path for making a decision.

HSA: there are two parts to this. The high deductible healthcare plan and the HSA account admin. For a healthcare charges up to your high deductible you would pay for it with your HSA debit card or electronic check. The amount still gets sent in to the insurance company so they can record it.

Once your deductible is reached then healthcare costs would still be sent to the insurance company, and based on coverage, the insurance would pay its part and any remainder would be paid by you, with your HSA account.

Any reimbursements issues would be with the insurance plan, hopefully not with the HSA.

I can purchase my own high deductible plan at about 300 per month. This would be for me, my wife, and three children. Family deductible would be 10000. We are all healthy and I have the cash in the bank to cover a 10000 emergency. If I wanted no deductible it would cost about 1200 per month.

When purchasing insurance yourself, you may need to purchase separate maternity coverage, and you may need to wait several months after starting maternity coverage to get pregnant. Otherwise prenatal care and delivery would not be covered, although the hospital stay and baby care would be.

Not sure if New York has this, but Maryland has a special small business insurance pool. It allows small businesses to buy employee coverage cheap. If there are a few people involved this could be the way to go. Going this route would require talking to an insurance broker.

Good luck. Wish you the best of luck with the new family if you go that route. I have three children and it was the best decision ever.

Glad to see that I get something for my high taxrate.

I think one downside to it is that it's hard to do anything out of the ordinary (ie some new drug or method or whatever) because health care is seen as a standardized gov't service. For customization, you still need privatized medicine.

Or am I wrong on this? I don't have a lot of insight into the health care system, honestly.

Of course, for this to work, there has to be a lot, possibly the majority, of super-payers who pay more into the health care system via their taxes than they receive back.

So, Scandi style health care can in a way be seen as a government-enforced mandatory health insurance, except that unemployed people get it for (almost) free.

Then again, a huge socialized health care system might have better economies of scale (or they might be worse). Also, let's not forget that people can go to medical school for free in Scandinavia, which is bound to have some kind of effect.

Yes... but, this is also true for for-profit non-socialized health care insurance.

The fact that Americans have to think or worry about health insurance -- and that they can and do go bankrupt when they cannot afford to pay for care -- is bad enough. The fact that many Americans then claim that their system is the best in the world, and needs only superficial change, is shocking on several fronts.

I was fortunate enough to have good health insurance several years ago, when my family was living in the US, when I did my PhD coursework. (We only got this good insurance when the university wanted to charge me more in insurance premiums than they paid me for a stipend.) When my wife got sick with something that's very expensive to treat (but was treated and cured, I'm happy to say), we were especially lucky.

Remember, all of you young entrepreneurs out there, that the odds of getting something might be small, but they do exist. You don't want to be without health insurance if that happens. Again, the fact that this is even possible is a uniquely American phenomenon, and a sad one at that.

Coverage? My life partner had CT, MRI, fMRI, little more than a week of hospitalization, and a brain tumor removed within a month by one of the top neurosurgeons (by Yelp-like recommendations) in Poland. Additional cost? None.

Can't imagine being a US citizen, working for a startup and that being an issue, especially if you have a family.

Yeah, it's nice to know that if I ever end up in a hospital I won't need to worry about what that costs, but don't make the mistake of thinking that our public health system means that private health insurance isn't a very good thing to have.

That said... if you're starting a family... pregnancy (and RX) are usually (ever?) covered. So you might not have a choice.

As a small business, if it's just you and your wife (and your dependents) you can deduct the premiums though...

> That said... if you're starting a family... pregnancy (and RX) are usually (ever?) covered. So you might not have a choice.

HSA's do seem to make sense, but the pregnancy and any potential complications were my main concern. It seemed from initial research that for this scenario, and regular plan seemed like the best option, unless you had a different experience? Perhaps use a typical plan initially, then switch to HSA's later assuming health is ok?

http://nyc.gov/hilink

Some of the lowest-cost options are offered through Freelancers Union:

https://be.freelancersunion.org/benefits/