Reenlisting is both a sucker bet and a good deal rolled into one. I reenlisted because of the money and because I enjoyed my job. I was discharged before fulfilling my contract. (spare me people....) Being on the outside looking in, I can tell you, you should REALLY try to stay in right now. Prototype is a crap deal... while you are still in the military. Go to a prototype, get watch supervisor quals as SOON as possible. when you get out, you can walk into an SRO position and make a ton of money that way. Rank doesnt matter when you get on the outside. E6's with watch supervisor experience get paid the same as 0-4's with watch officer experience.
You NEED two years experience of standing watch sup. You can also get ancilliary quals to help you be more hireable. One thing I learned from the navy.... NEVER pass up the opportunity to better yourself. While you are at prototype you can get a degree as well. It really boils down to your motivation level.
So bottom line, you have several options. 1) stay in, qualify PPWS, make chief, stay in. 2) qual PPWS, get out, work at a civ plant as an SRO for 100+k a year. 3) get out now, hire in as an NLO, make 70k a year that will only go up. 4) get out now, get your degree, hire in as an NLO, make 70k a year blah blah 5) do something different....