Try this one - - my family have their health insurance in NYC - it is affordable and has good coverage for dental issues.
As I remember they can provide such a service.

US News did a survey about Top insurance companies in USA.

Here’s the link to US News site:

You can get a better perspective straight from horse’s mouth if you can call some of the top players who can in turn guide you in the right direction for your needs,

see this one form to get a number of quotes from different insurers. You can even bundle it with car insurance, good luck

You seem like a good friend.

There’s a very good article at eHow that discusses how to get health insurance when you don’t have a job that covers you:

How to Get Health Insurance

Take a look at it, as it covers all the major possibilities for getting insurance, and gives some great resources you can use.

If money is a big issue (and when isn’t it?), you can also look here for tips on earning some extra cash online:

How to make money on the internet, scam-free

All the best.

You say he’s NOT a citizen? That’s an easy one…have him apply for FREE everything at any Social Services Office!