I'm thinking of remustering to a new trade (switching jobs within the navy) since I think I've gotten about all I can out of my current trade in terms of the stuff I actually like; even if I climb the ranks, IT Monkey positions are in short supply, and as you rank up it is very administratively-focused and the only exciting part is radio spectrum management and maybe a little bit of satcom administration. And by "administration" i mean that seriously, lots of paperwork and meetings.
Should I go
>Combat Systems Engineering (local electro-mechanical handyman technician when they can't fly a Lockheed contractor in)
>Combat Information Systems Operator or Aerospace Control Officer (detection and target resolution for surface and airborne contacts)
>Intelligence Officer (OSINT collator)
>Logistics Officer (logistics officer)
>say fug it and do subs for more money in my current trade (will have to quit smoking for those more-than-three-day dives)

I never took my GI bill equivalent free school money so I was thinking of picking a new trade, taking courses essentially for that trade, going either officer or at least high-paid technician once I have the degree, and then having both the degree and back-up plan of staying mil forever.

And more than that, I haven't said this to my own bosses; how to I approach my boss (who is quite gung-ho about the trade) and say "I don't like what I am doing. I have reached the limit of what I can do usefully, or at least the limit of what I genuinely care about and can do in confidence and good spirit; there's a will, but there's a void. I'd like to shadow a couple other departments in preparation to quit."