I think after 5 years of military service as an officer and a military academy EE degree you could easily obtain very lucrative military contractor work, but of course this is generally going to be in the weapons/electronic warfare sphere which may or may not be ethically compatible to some folks.
The two aren't mutually exclusive; you could easily get contractor work with five years of EE after going to another school (provided you can pass the background and security checks).
Absolutely, but if they're hiring for the last slot and you're up against a USMA grad former O3 (probably still in the reserves, too) that's very tall hurdle to clear.
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