TreyLagger,
As you said there are many variables. At a minimum you need medical coverage. Depending on the benefits for your dental and vision care, you may not need coverage, as the 'savings' could be a wash. That is the cost of premiums and out of pocket are higher, the same, or slightly lower than going without coverage and paying from savings or an HSA.
So as Michael indicated, the formula you need to account for is deductibles+out of pocket (co-pays)+premiums. That's the total maximum cost to you each year, based on what you use now. If you have kept your claim benefit statements (commonly called EOB's), you can see what your doctor bills, and what the company pays, and your out of pocket costs. If not, they are likely on-line at your carrier's member website.
This was my experience, and I worked in the health insurance industry. I retired at age 59. Note that I am not an insurance agent, so this is just my experience.
To help you decide, you need to compare your benefits to what's available - including premiums. I too had an employer subsidized plan. I found that the coverage was broader and the premium the same or slightly lower than what I could find with private insurance.
To start your comparison:
* One way is to contact several carriers and have them send you individual insurance packets.
* A second way is meet with an insurance agent to review what you have and what they sell. Most are very happy to advise you, whether you buy from them or not.
* A third way is to use the ehealthinsurance.com website. This is an insurance agent licensed in all 50 states. You will get several quotes, and can use their customer service for questions if you feel comfortable in doing comparisons by yourself.
At an agency, online, or with an individual carrier, when you call to discuss, you are speaking with a licensed agent. Some get compensated directly for selling to you, others get compensated by the work of their team in making sales. Don't let the compensation issue stop you, they all want to help! In the individual market, generally, people who talk on the phone earn salary and commissions. It's how they are paid, and the payment is factored into the premium and is not something you can avoid.
At your age it is beneficial to consider an HSA, especially if you and your family only use the minimum wellness benefits. The HSA creates a tax credit for you and has you socking away a good amount each year to use after you go on Medicare.
Review your options with your employer. You may be able to switch to a different plan when you retire, they may offer an HSA. There many options, but the first step is knowing what you have, what it costs you, and whether it is worth switching. In my case it wasn't worth the switch as the benefits were broader.
Best of luck,
Rita