I I guess what I can ask is that what you experienced guys would have done in my situation?
Here's what I did: Added a commercial SE, ME, and Inst to my existing Commercial Rotorcraft Certificate. Earned my CFI, CFII, and MEI. Instructed part time. Took my 700 helo hours at the time, added them to 500 airplane hours, and was hired at a part 135 freight company. Had 1000 ME PIC time in a year and 2000 TT. From there I could have gone to the regionals, other 135s or corporate. Most of the guys I flew with then are flying corporate-ish type jobs now. Some are regionals or air ambulance. I got out of the civilian side and eventually worked my way back to helos in the National Guard.