I am also insured through hub's insurance from his "day job" - and we recently switched from a Blue Shield HMO to a government-based Blue Cross PPO and I love it. It costs a little bit more (about $500/month for 4 of us) and there is that $500/year co-pay per individual for non-regular type costs (for example: hub's asthma treatments, etc.) but compared to an HMO it's WAYYYYYYY worth it.
For example, my sister gets IEHP (Inland Empire Health Program) from the county out here in California - a free/low-cost kind of medical care program from the state... her coverage is better than the HMO we had before that we were paying $425/month for... I had a knee injury that took 5 weeks for MRI approval... she had a turned ankle and got an MRI the same day....
I think a webmaster insurance program is a great idea - I hope you guys pull it off. I know there are many who could have benefited from this over the years...