Who to contact?

I suggest you send it to the head coach however I don't any reason not to cc: the assistant coach on your emai as well.

Thank you jersey dad. I've been sending it to the head coach in most cases but today I was sending one to a school and the email had no relevance to the head coach at all so I sent one to the assistant instead.

I would send it to an assistant coach since they are going to be the ones out on the road recruiting.

Send it to them both... I always do just in case. There are some schools that don't list the head coaches email so you will have no choice. It won't hurt and I don't think you will be offending anyone.
Merc

I agree with Coach Merc. Go to the schools website and look up the recruiting coach.

Coach Merc? I just followed the link from your post above. I feel that any coach worth their weight in coaching and caring would pass along a starter packet including the four topics listed in your link. http://allbaseball247.blogspot.com
From a Players Perspective,Transitions,College Visits and Just Links would be more help to a prospective athlete and the parents than anything a coach could possibally say in a meeting prior to the season. I would hand them out at tryouts to get the players and parents on the same page as coaches and each other. Awesome information! I will pass them on for sure!!!

A hint with regard to finding coaches email addresses. If you cannot find the email you want on the baseball site - remember the coaches are employees of the school. I have found many actual individual email addresses by accessing the faculty / employee email index on line. Good luck!

IMHO I would send initial correspondence to the Head Coach. If he directs you to the asst or recruiter, then so be it. I'm partial to the HC for a couple reasons:

1) He is the final decision maker in almost all cases. It is his program.
2) Asst coaches and recruiting coaches tend to change alot more frequently than HC.