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Thanks for sharing your personal situation. I imagine there are a lot of folks who feel similarly about their work/life situation. I have been in the Navy for 15 years and while it has been rewarding it has also taken a toll on my family and me emotionally. I would love to be able to take a little time off to travel or work in a job that was less demanding.

I think all your ideas are great. Another option you might consider for some side income is teaching at a community college. The requirements to teach at that level are much less than at a full university and it could be as little as one or two classes a semester. Another potential option is getting certified to teach with one of the online colleges. You can usually work from home and don't even need to live in the same state as the school.

Best of luck as I contemplate my own transition in about five years. Fortunately for me a 20 year stint in the Navy comes with a pension so I will have a little flexibility.

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