I’d rather ask questions and have a strategic plan to be more prepared than my classmates rather than get caught off guard. But I appreciate your help.You're worrying about the wrong things here. Ultimately, you have very little control of where you go once you get to OCS. You need to make peace with that and stop trying to work the system right now. In fact, you will likely have little control over where you go for the next 8 years of your career until you make your bones as a department head and start getting slotted into the OPS, WEPS/CSO, CHENG pipeline. This is because you are a prospective JO and haven't gotten enough experience to break you apart from the thousands of other junior SWOs. That won't happen until you're a department head, at which point the powers that be will start racking and stacking the senior O3s and O4s to get them ready for command.
But don't worry too much, your class officer and/or staff officers at OTCN will likely have the inside skinny on where the ships on the available list are and what their schedules look like. Worry about that when the time comes. Also understand that the ships that are available now, likely won't be available when you get to OCS. My class didn't have a single ship available in Norfolk, and I didn't even get to choose since I was up for orders at the same time that the Academy kids were doing ship selection. You could very well end up in that same position so there is no way to plan right now.
It's not exactly random. I could have gone and become a submariner, but I have/had no desire to ever become a Nuke. Also, due to funding, resources, manpower, etc. it is not practical to give every single recruit a full form flight physical, hence you get a basic DODMERB at MEPS and then get the full work up once you get to OCS. Really, you have to make your peace with the fact that many of your career decisions will be at the mercy of the Needs of the Navy™ from now until you walk across the brow for the final time.