My advice to you: Contact an indepdentent
insurance broker in your area who can help you sort out all that stuff. I'm a broker in Missouri (and a few other states, but not NY). My first question to potential clients is, "Do you belong to any professional trade associations who offer benefits?" If the answer is yes, I encourage them to write for a benefits kit before going further with me. Once they have the kit in hand, I sit down with them and we compare plans. Associations can often beat out what prices I offer, and in those cases I encourage the applicant to pursue the association plan versus what I've got.
That's not always the case. I've seen some crappy plans from associations, too.
A broker is free to you. It's worth getting an opinion from one of them.