OK, I feel that I need to put in my two cents....
Get a full time job at Simuflite or Flight Safety.....
Build a client list out of your sim clients... "Hey, if you ever need anyone feel free to call me...."
Work your ass off at both jobs....Continue to build your clients....
When you are ready, go part time at Simuflite or Flight Safety (Guess who pays for your currency training???)
Insurance can be handled by: your wife's company or your own policy (It only take about one days flying pay to pay the premium every month)
for a kicker, you can join the reserves and fly part time for them. So lets review:
1) I control my schedule
2) I have a pension thru the military
3) I get insurance thru my wife
4) I have a list of clients who pay me 400-500 dollars a day mostly out & backs with the occasional vacation type trips (OK I like to gamble every now and then)
5) Training is paid for by someone else (Some clients have also offered to foot the bill)
6) I have diversity in both where my income comes from and what my job is like.
7) Self employment tax is something to think about, but, you also get a butt load of new tax write offs that can offset the income (Home office, furniture, flight simulator, new headset, etc....)
8) Income that is in the neighborhood of 100K+ while paying very little in taxes.
9) I go home almost every night except when "I CHOOSE" to stay out.
10) Quality of life that most people only dream of in the flying world.......