Your best bet is finding mentors to help your process along, your ccc makes sure everything is submitted correctly, in right format, waivers included if need be. You can “ask” for advice but street applicants process is wayyyy different from fleet applicant OCS. They don’t even have the same processors. Putting the package together itself is mostly you getting all awards, evals, schooling, letter of designations together. Any questions outside of that can easily be assessed. Trust me and find your a few mentors that would be willing to look over your package, personnel statement etc. Find out which board you want to apply for, give your self a deadline , make arrangements to take the oar if you haven’t already and trust the process