I was involved with the JR squad of a largish local team while my son
was coming up through the JR ranks. Here are a few things to consider.
First, I agree with Dan, if you have a JR team nearby, they'll be able
to help you tremendously. If not, there are other options.
Most local clubs have weekly group rides and some have local training
races as well, though they may not have JR-only events. If you can find
some local adult racers, they may be more than willing to donate some
time to mentor a younger rider. Having him get into some group rides
will do great things not only to build his skills but also his stoke.
If a kid started feeling fast but his group riding skills were still
shakey, we'd usually start him out doing time trials - a good option if
the club has 'em. If there is a weekly training crit, having a SR racer
ride with the JR creates all sorts of teaching opportunities.
If there is no local club, sometimes bike shops sponsor weekly rides.
With regard to jumping right into races......if your GS has a road bike
& loves to ride, his enthusiasm is by far his most valuable asset -
that's what you need to feed. Depending on his age, fitness and
expectations, jumping right into a race may or may not serve that goal.
In general, the younger age groups (10-12, 13-14) are much more
forgiving for inexperienced riders than the older groups.
Bottom line, road racing is a really social sport that brings together
a pretty diverse group of fit people. It's a great scene to be a part
of, but might not seem all that welcoming to a shy 16 yr old who lines
up with a bunch of kids who've been racing for 3 years and who promptly
drop him like 2nd year French. Might be better if he has some clue as
to what it's all about. I hope you're able to hook him up.