First, welcome to RC Universe. This site's members and most people involved in RC flying are pretty terrific. And the folks here will provide answers to just about any possible question. Take the advice you receive here, it will serve you well.

If you've "been intrigued for years", and your son has been expressing interest for a while, then I'd advise you to go the 40 size glow trainer route.

This WILL entail finding a local club and an instructor, but the trainer would work great for both of you. (I'm currently instructing a father and son on the same trainer.)

Don't be surprised if your son does better than you from the get go though. Kids typically have better hand/eye coordination from playing video games, and if he's ever had an RC car, he has a leg up already. (Turning while the plane's coming toward you is counter-intuitive and takes a lot of practice before it becomes natural.)

You can get RTF trainers for about $300, and will need to spend about another $100 to get all the support equipment necessary to get going.

I'd recommend finding the club first, and speaking with one of their instructors in order to get his input on radio equipment. In order to use a buddy box, your radio gear will need to be compatible.

Below is a link to the AMA's website. (A national organization that provides liability insurance and a lot of other benefits.) Most clubs require AMA membership in order to join, and for instructional purposes.

The site also has a page where you can look up all the clubs in your area (by zip code).

http://modelaircraft.org/templates/ama/

Please don't try to go this alone. It will prove to be costly and extremely frustrating for both you and your son.

Good Luck,
Dennis-