How much will I pay in health insurance with a 50 percent tax deduction?
If you're in a 12% bracket, the deduction will make up for $24 a month of the cost. This would leave you paying $376 assuming you can find a policy for that same cost as your employers group rate. In 24% bracket you'd be paying $352 per month of it.
Your costs for coverage will change...you no longer have that plan...so you need to research other plans. Once you find a plan, take off 50% of the premium and go from there.
Why only 50%?
Since you are (NO) longer an employee, then the employer won't pay anything on your health insurance. As an independent, then you are self employed, my guess is that you will need to buy your own (private) policy, thus suggest you talk to a CPA.
Unknown. See if there are any industry groups you can join and get insurance through them. Buying insurance by calling up the insurance company means you pay the highest rates of all.
Unknown, even if you are with the same company, you can't assume it will cost the same. Call them and see.