My son is also 14 but he is a Freshman this year. There are several questions come to mind that you might need to consider. What does he are his interests, what career does he want. In 8th grade they had him take a interest assestment test to key in on what he would be good at or what career his natural interest would lead him to. If your son's school does not offer this, then the High School Counselor should be able to assist him to a career field he may be interested in. From there of course is to keep his grades up, be involved in the extra cirricular activities in school - including those things that he seems to want to interested in career wise. The High School should help in in what courses to take and such. If he is not for sure and is all over the place, have him consentrate on the geneneral courses (English, Match,Science, History) and as his freshman and sophmore year passes have him look into several difference career fields to see what might interest him.
In his junior is the big push to find scholarships, grants, and the like to help fund the college. The High School should have the resources and the internet is also a good resource to look up information.
My son is interested in the medical field and so this summer I will be looking for a hospital or clinic for him to volunteer at to see if this would be a working environment that he feels he's suited for. Something like this could work for the field your son is interested in also.
If you are budget minded and frugal. My son plans to do two years in a community college and the last two year at a major university (unless he gets a direct scholarship). It is the University that you finish your degree in that gets placed on your diploma not where you took your basics - his plans are to go to Baylor. I have been told that it some times is easier for a transfer student with excellent grades to enroll in a major univerisity as a Junior than it is to get in as a freshman. I throw this out as something to think about.
His GPA and extra activities are the focus. Many colleges and university are starting to rethink the way the evaluate potiental new students. As for now, pre-AP course are great but it they are too difficult and pull down the GPA, it may be something that needs to be considered. Again the HS should be keeping abreast of the changes in recruitment for the universities and what they are looking for. I wish you the best.