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Interesting discussion on this thread. I'm pretty impressed that you looked at the cost benefit of the Masters prior to pursuing it.
I made my decision to pursue my first Masters (in Systems Management)from an on base program with Florida Tech right about the same time I decided 20 years would likely be it for me in the military (that was at the 16 year point). The Navy picked up 75% up to $3500 per year but with the time frame I was shoving my studies into I was out of pocket about $3200 for the program. I also owed the Navy two years after completion, which they require of Officers, so I wanted to ensure completion at the 18 year point. At the end of that period I found that I enjoyed the learning so much I continued with the 7 extra courses required for the "Professional" MBA also from Florida Tech. I have found the "Professional" to be strictly a marketing ploy as I pursue employment opportunities. Employers seem to be interested in the MBA but the "Professional" makes them wonder if this is, as has been stated previously on the board, an MBA Lite. Because it is a traditional MBA I have dropped the term "Professional" from the resume because of the confusion it has generated. This second degree cost on the order of $7000 with no TA. Clearly I didn't do a great CBA of it but nevertheless really enjoyed the learning involved. I guess we'll see if the benefit long term will justify the extra cost. I certainly hope so.
Finally the discussion on the fact that we Military types can "only provide 25 years with a company" is becoming outdated in the world. People are churning jobs at a rate of about every 3-5 years. I don't know if that is significantly more prevalent in the High Tech sector than in traditional industry but I have seen signifcant evidence of this in my job research. Our issue as Old Fogey Retiree Types (or in my caes soon to be Retiree already Old Fogey) is that employers ARE looking for young people with little outside pressure (ie family) in order to work the h*** out of them while their wage requirements are relatively low. We just have to sell our assets which have been well enumerated on the board.

Probably too long but I had fun writing it
With Respect David
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