When my son was a senior there was a special ceremony for all of the student body that had earned scholarships of any kind.
There was one student inparticular that received scholarship after scholarship . This was a kid that always did well academically and was a good athlete as well. Somehow his family figured out the keys to the gatekeepers. He concentrated on academics, excelled, and I am sure from my count at he ceremony he had well over $100,000.00 in scholarships from a variety of sources. They knew what to apply for and applied for many, many scholarships, mom said it was a part-time job for her, but hey it paid off. They did not put out a lot of money on travel teams, etc. instead they went the academic route with very nice results. The kid now plays intramural/Rec through his Frat at his school - he has the best of both worlds.
Check out this book for some assistance:
http://www.quintcareers.com/career_book_reviews/Gatekeepers.html