I did it for the last 8 months. Insurance isn't a big deal because all Ive had to do in the past is fill out a pilot questionaire for whoever it is ill be flying for.. (you know the form... total time, pic, sic, etc....) Tax wise, I always planned 25% for every dollar made would have to go towards taxes.. Thats probably a little heavy, but fighting the IRS is a losing battle. I always tried to be fair with my daily rates. Dont get me wrong I wasn't below average or anything but I always tried to be fair and negotiate. If this is going to be your only source of income, you don't want to piss anyone off right off the bat. I found a full time job recently due to the fact that my currancy in all my types was about to run out. Recurrent training is not cheap. (I am sure you know that already) It is, however, a write off. But its a large upfront expense. I was covering 3 different types and school was very expensive. Good luck