I was in your shoes 20 yrs ago. The short answer to a long story is that in my day field accession boards were few and I was a Major before my first (and only) opportunity arrived. Granted, I was an NFO and the move to being a pilot would have been back to my original community, so the lat move would have been less dramatic than moving from the 06 community. However, I realized that had I been selected, the move would have killed me for promotion for many of the reasons that AMG pointed out, but I was willing to accept that. Without the accession board, I followed a plan similar to what you've outlined to get my civilian ratings and acquire the needed flight experience through instructing and recreational flying so I could qualify for the airlines in my post-Corps career.
Now, I have all the ratings and hours to be competitive, but I chose not to pursue the airlines for quality of life reasons. Instead of flying professionally, I use the skills I acquired as an officer to work for an awesome small company with very flexible hours and great pay. I recently purchased a T-6 that I fly recreationally and I'm building an airplane in my basement, both of which are life-long goals that would not be achievable at this stage in my life had I gone to the airlines.
This was a long, long decision for me with lots of input from others who are flying for a living and not flying for a living. Most of my squadronmate pilots fly for the airlines, and most of the NFOs work in corporate America. Several of the pilots were furloughed post 9-11 and opted for alternate careers during the down time. About half of them decided not to answer the recall when they eventually were called back. Many of the CFIs that I worked with over the years have made the transition to the regional or corporate world. Also, a lot of the discussion on this forum helped me shape my decision.
In the end, my decision came down to quality of life. I wanted to work somewhere that valued me, not somewhere that I thought management was out to screw me. I wanted to be a valued member of a team and make a valuable contribution to society and enjoy the work I did. In considering my options, I'm not sure I'd ever have the QOL in the airlines that corporate America offered me on day 1. Although my pay and schedule at the airlines might catch up in 10-15 yrs, I'd never make so much or have such a great schedule to recover the lost wages and time in comparison to corporate America. Pursuing my life's aviation goals was more important than earning a paycheck as a pilot.
YMMV
