Ideally, parents should begin the process of learning about the college admission processes and standards BEFORE their kid begins HS. Of the thousands of potential colleges, the number needs to be winnowed substantially. Eventually the result is an intersection of academically suitable schools and baseball schools - but academics are far more critical early because of potential baseball attrition.
So, a family should set up an appointment - as early as possible in 9th grade - with the school GC. Learn what curriculum are offered, what colleges look for (e.g., a kid taking the "most rigorous"), what extra-curriculars are desirable, where that HS sends its graduates, etc. If this is your oldest child, this is a long - and constantly evolving - process. (DO NOT LET BASEBALL INFLUENCE ANY STEP IN THIS PROCESS. All sorts of things can derail totally a HS baseball career (girls, weed, desire, injury, whatever), up to his last game; an academic record is built over a four year period and can't magically be created overnight. (Many schools have computer programs which, e.g., can display the college application results of all its students in cool easy to understand graphs. These programs are huge helps.))
This gives a start to understanding how a kid can and should be positioned to maximizing his college options - from the HS performance side.
Also early in the process financial constraints - if any - can be identified. These constraints need to be shared with your child. There may be some financial planning early in the HS process which can result in more FA when the time comes.
In a perfect world, parents should have a handle on their kid's academic performance - recognizing that just because a kid was a stellar MS student doesnt ensure a stellar HS academic record; but a kid who struggled in MS will most likely not all of a sudden become a great HS student. With this educated guess in mind, colleges that suit his academic perfomance can be identified and further researched. (I am NOT saying to look for any specific majors; I am saying look at academic profiles of the average student which are found on the colleges' CDS.)
Also early are visits to all types of colleges - big, little, rural, urban, north, south, etc.- will eventually lead to discovering which type of college is preferred. (Recognize that college preferences may dramatically change during the process.) Try to go to some college games to see the level of play.
IMO, you've got a cart/horse issue. Everything you're asking has a baseball overtone (9/1 junior year, OV, etc.). Winnowing the 1000s of choices to a more manageable number occurs without any baseball consideration - because NO ONE KNOWS WHAT LEVEL OF BASEBALL A NINTH GRADER OFFERS. (My son was about 5' 4" 115 lbs in ninth grade; there was no way to see the baseball path he eventually followed; but, we knew - from meeting with the GC what would be his most likely courses for his HS career.)
By focusing on baseball and developing your entire college approach - IN THE NINTH GRADE - on baseball means you are most likely burning options from which decisions he can't recover if baseball doesn't pan out. (And, if you're not spending the same mental energy on his academics as you spend on pre-HS baseball you're betting a lot on something which can be derailed in so, so many ways which ultimately will come back and bite the person you are seeking to help.)
The long and the short is this (and applies for athletes and non-athletes): it's never too early to be learning about the college process. There's lots to learn and the time just seems to fly. The later you discover critical information means the fewer options to address that new info - and there is always new info to be absorbed.