RedEye, Though I have major reservations on anyone encouraging a kid into a life of gambling, I can't be a hypocrite, as I began at 14, and come from a family of quite a few Pros & BMs, then spent ten years with a working piece of a betting office, during and after college.
In today's world of gaming proliferation, many parents are in denial, if they think that their kid isn't going to be in card games, casinos, or having sports action by the time he enters college, so I agree with you mentoring him..get his action-jackson in check, then again at only $20 per game may be the best way to learn.
In my first fall of betting the NFL, I not only won small for the fall(playing only my top 2 or 3 each Sat/Sun), but also was one of only about 5 that picked Oakland over Philly in SB-XV, with a score of 24-10(missing the 27-10 final by an FG), and bringing home a SB Party pot of $500.
Earned my allowance as a teen, by keeping my father's pitcher's baseball log books up-to-date, making game lines each day/week by using different power-rating numbers, reading and condensing down newspaper articles, making schedule blowups at copy shops, making square-up payments and pickups,etc..
We all have to take our lumps, his learning curve has begun.