More competitive colleges will pay attention to how competitive your high school is. And the ones in your state will no doubt be familiar with your high school. But it’s more important how rigorous your own group of courses is, and how you did in them. Your high school’s competitiveness can add some context, but that’s it.
I don’t see how your family friend can help that much, other than giving you some insight into how that school’s admissions works. (You should have asked him your first question!) Few colleges want letters of recommendation from family friends, no matter who they are. And I’m not sure it will help much to have him call a former colleague to make sure they consider your application. They’re supposed to consider all the applications, and asking for special attention might not be appropriate. It’s not like applying for a job, where you could ask a family friend to make sure your resume at least gets read by a person, and not lost in the online application system. Even if colleges don’t treat all applications the same, they at least pretend to.