As an additional perspective, while planning some of this stuff ahead of time is great, stand advised that once you're in Newport, your plans mean absolutely jack shit.
I saw people, especially pilots, that didn't get orders cut at all for days, weeks, and even in some cases months after their class had graduated due to any number of lingering issues, but most often obscure medical stuff. I saw people NPQ'd from flight the night before graduation that came as a complete surprise, and spent months trying to redesignate. I saw people that literally did not have the time to finish all of their screenings at OCS and got stuck their an extra week or two as a result because their class team was a bag of dicks to them. We had most of a class ahead of me get stuck for a week while the Navy dug around for money to send them out. Some people were just late getting orders because they were slow in processing them. In any of the above you end up stuck in Student Pool, which is essentially OTCN slave labor. Depending on your status you may or may not get your commission prior to entering the Student Pool. We had people from early in 2015 still in Student Pool when I graduated in mid 2016.
I also saw approximately 1/4th-1/3rd of all students that went through OCS during my time roll into a lower class, often for reasons utterly beyond their control, including ten year prior service members that were CFL's, prior service members that maxed out PFAs, college football players, and even guys that swam against Michael Phelps. OCS is a really strange place, and any number of stupid things can get you kicked back weeks in the process. Food poisoning, possible illness, injury, a perceived lack of enthusiasm (Fast Cruise), simple DI/RDC whim (RLP), can all wreck your plans. I saw someone have to start over six days before graduation, two people get kicked back 3 weeks in the process two days before graduation, and countless talented, fit, committed people forced to repeat evolution.
Morale of the story: get ready to be flexible, both with your graduation timeline and your post-graduation timeline.