Most of aviation deals with famous "Catch-22" scenario. Can't get a job without hours and can't get the hours without a job. See the movie or read the book - a must for any career pilot. It just takes persistance and hunting for opportunities like you are doing. I got out of a major college flight school in 1988 with about 300 hrs. Beg, borrowed and stealed (not really) hours while I worked a "normal" ground job with an airline. Got to about 500 hrs before I went for the CFI and renewed every 2 yrs with another (CFII, MEI). Competition was tight and I didn't get a steady CFI job until 1992, but I was still contract and picked other work where I could. Airline hiring had taken a dump so I continued the contract flying gig. Tried for a regional in 1996 when I had my ATP and if I remember right about 2000 hrs and 200 ME. Turned down, still not competitive on ME time. Got on with small air charter/air ambulance for a year. Still no turbine opportunities so got a C-208 night freight job. By this time in 1998 the regionals had been booming and now I was almost over qualified at 3000 and 800 ME. Finally got a local corporate/135 job that I had been after for a year and a half, but still by being the right person at the right time. Got an interview offer at a fractional the same day I got this job. Bird in the hand worth more than one in the bush and turned down the fractional (also got engaged same year). Got promoted and now make as much as most captains at the regionals. Of course I may have to pound the pavement in the (near) future and if lucky to get another job, take a pay cut. All it takes is blood, sweat, and tears. But enough about me.
Insurance hit the small turbine and 135 operators hard in this past year. For our insurance on (our only aircraft) a 1996 BE-B200 with 50 million liability, 2.5 mil on hull, "open" pilot requirements of: yearly FSI or Simuflight, PIC with 3500tt/2000me/100 type, required co-pilot now with 1000 tt/500 me/25 in type - we pay $32,000/yr. Ridiculous - yes. Of course with a qualification review the insurance carrier will take less hours and the pilot has to be "named" on policy. This is with USAIG. Any other suggestions for insurance carriers?