I lost my individual health insurance policy this year, and just signed up for another one. The only actual insurance company left in my state that does individual policies (not an HMO, etc.). Of course I’m paying for it (50% more than last year just on the premiums). I had contemplated becoming a “corporation” - but it all seems pretty complicated for a one-man outfit like me. I would need to pay myself a wage every month, keep all the records, fill out the various forms every month, etc.
I believe that this new bill won’t even allow me to deduct my $29,000 a year medical premium, so I’m getting screwed both ways. I guess I’ll need to incorporate. Of course I’m screwed triple - unless they allow “new” corporations to purchase health insurance outside of the Nov - Dec window.
I knew a guy who was a sub-S for many years, it’s not that complicated. His billing rate was about $900 a day, and he got to write off many things he could not write off as an individual. His accountant told him how aggressive to be, but he definitely took his medical insurance, one car lease out of two, and a lot of business lunches. He also had the flexibility to let money build up in the company, and pay himself when he wanted.
You should at least investigate this, and see if it is suitable for you.