Hi, CTI2 here. Like CTT1 says, it really depends on the language. Some have no opportunities for certain types of dirsup, others are a little bit more open. Your chances to go to sea are better if you stay in past the first enlistment - for Chilings it's less than 20% for E4 or E5, but about 50% as an E6.
You can look on the community manager pages to see the breakdown for a specific language family - "sea" includes ships, subs, and aircrew though.
Of the dirsuppers I know, most go out for a month or two at a time. Longest I've heard of was 9.
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