If it is set up as a small group plan, the employer can either pay for the premiums, or set up a Section 125 cafeteria plan and allow employees to pay the premiums with pre-tax dollars. This can be done regardless of whether the employee selects "employee only" "employee+spouse" "employee+children" or "family" coverage.
If the employees purchase the coverage on their own, outside of the business setting, there MIGHT be a way to legally reimburse them for it as a business expense, but it would probably require setup of an HRA (Healthcare Reimbursement Account) which would be specifically set up to allow health premium reimbursement, or some kind of other setup that might allow it (I don't know, and doubt whether it's worth the hassle and expense for just one or two employees).
In NY, unless you want to take subsidies (which many people don't) whenever you have a choice you are much better off doing it as a small business group.
So, to continue an old conversation..
I looked into it some more, and it seems an HRA is the way to go, and it can be pretty simple to set up. I found a company online coredocuments.com that sets it up for you for $150. It can save me 2-3k per year. in fact, iiuc, it's only really feasible if you have only 1 employee (or more if they're all family).
Anyone have experience with an HRA?
Also, I'd like to do an FSA for dependent care in an scorp where my father is the owner, and I'm the sole employee. Anything I need to be aware of, or just simply set it up, and do I get to avoid FICA?