Currently finishing up my commercial and trying to decide between spending 30-50k on an airplane to fly random cross countries or spending 1-3 months getting my CFI/CFII and going from there. If I bought a plane, I'd likely try and get a low time job around the 500-750 hour mark. I'm in my early 30s, no debt, not married, with money to do either.
I'm also kind of unique, in that I already have roughly 8 years or so of non-flying Part 121 operational auditing and safety program management experience along with a masters in aviation safety and an aircraft dispatcher certificate that may make me a slightly more attractive low time candidate than someone straight out of school. (If you want to know what "operational auditing" experience means, check out AC 120-59B
http://www.faa.gov/documentLibrary/m...AC_120-59B.pdf). I was reasonably good at my job, and my experience with regulations and dealing with the FAA could likely be a huge plus for some 135 operators. Since I'm largely trying to focus on flying now, that's the kind of thing I'd only agree to do part time though.
I know there's pros on cons to each, but I at least feel that if I didn't choose to get my CFI, "check-mark wise" my previous airline experience and education would likely more than make up for it.
Just curious, what would you guys do if you were me?