OCS package
Ok, to start, I just went through the exact same issues you are facing. I spoke with a former board member who was happy to bestow some of his awsome knowledge. He told me if I didnt submit my package ASAP, I was DUMB!
Here was his logic, if you got a package together, do it, get accepted or passed. The board gives a little hoot if youve ever applied before or not. Just get the damn thing in, make sure its solid and run with it. But be sure to definitely have a good letter of rec from the CO. As for your questions:
When are the best times to submit a package? when its ready
How do I know when packages are looked at by SWO, INTELL, INFO WAR, boards? Sorry, can not help on this one
Does it help my chances since Im enlisted? I have to say yes, there is always good reasons to promote with in. Your knowledge will help shape your fellow officers on the way they shoudl treat enlisted as well as giving you the ability to help your peers with the questions they will have as junior officers.
What are the most common mistakes made on an OCS package? dates, and format.
What are the board memebers looking for in the essay portions? Honesty, and cut to the chase, do not blow smoke up there rear.
Good luck!