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No! Contrary to what's out there, you can start an online business for little to no upfront money.
There are a lot of options, including affiliate marketing, content creation, UGC, just to name a few...
Yes! You just need a few hours per week to think of content, shoot videos, edit, and post. Some people get by on just 2 - 3 hours per day.
Were you guaranteed a duty station off your dream sheet? Hell no. Any business venture involves risks. And there are no guarantees for your success. I cannot determine your dedication to start a business nor can I determine how much effort you put in. What you put in is what you get out. With that being said some of the programs do offer a money back guarantee. Check each program before signing up.
I suggest you start AT LEAST 12 - 18 months before separation. If you're already separated or a dependent, then start now!