I do pay from my pocket for health insurance. We do not your 100% situation and advising to our best and it is soley your decision.

Do you do your own taxes? If you do still you will not know about how the self emplyee tax filing works.
How much benefit you will be getting? Have you calculated yet? If not , this is how it works.

Lets say you'r an independent cotractor :
You are going to use an office or part of your apt as office? If the second one to save money :
you have to calculate the Usage for office and you can deduct it as expense. If you own a house No tax specialist will advise to deduct your home for office use. At the time of sale the use of office need to dig back to calculate if you were in loss or gain while selling the house, I mean it will be added back. You can not deduct what ever you want _ there should be track and evidence in case you were audited.
If you are trying to establish yourself as independent contractor , have some free time and work on own schedule that is good.
But you will be looking for a job one after another then stick with W_2 , it will be easier on interview ( you may have to explain what happen and why you trying to be a employee ).
We just explained the difference between 1099 and W-2.