... by the time he's well into his teenage years that I'd have to use a combination of physical size, followed by intelligence, followed by financial leverage.
Yeah, sure, good luck with that. The only assets you get to have are a whole lotta patience & stamina.
Any object or activity confused as a conflict with parental authority immediately becomes overwhelmingly compelling, even if they normally would be disgusted by it. Mix it up with sex/drugs/rock&roll and you're lucky if you win one out of three.
I may be occupationally biased, but I think the best parental guidance is in Sun Tzu's "The Art of War" where he says that victories should be won without fighting any war at all. Use their emotion & angst against themselves. Merely the threat of embarrassment in front of their friends/teachers. Parental zen & jiu-jitsu.
Lately we've gotten some mileage out of "Well, let's talk about all the things that could happen and you decide what you want to avoid" and "It's not whether your mom or I think you should do it, it's whether you think this is the best way for you to achieve your goals" or "How well has that worked out for your [unemployed or pregnant or awaiting trial] alleged friends?" I especially like "How many hours would you have to work at your job to afford that?"
An interesting educational tactic (we're still working on it) has been our parental "AP Classic Rock History" series. Any commercial sound track or a movie cameo is fair game for an e-mail followup with the story behind the song, the lyrics, and a YouTube video link. Salacious behavior is a bonus. While she's rocking out (or laughing at the outfits & antics) I point out how Steven Tyler or Janice Joplin or Keith Richards or Rick James or Eddie Van Halen or Alice Cooper spent a large part of their free time (and money). The "Well, they turned out OK!" defense is met with a cataloging of all the family, friends, & fortunes they lost along the way. I think I really scared her when I told her that Keith Richards' cameo in "Pirates of the Caribbean" was done using his own hair and without any makeup.
A couple years ago an 18-year-old acquaintance of ours had a fight with her parents, moved out, and asked if she could stay with us for a few weeks. She used to ride dressage with our kid but now that was out of the question-- she spent all her time looking for a room to rent, working the KMart midnight restocking shift, dealing with a dying truck transmission, and struggling with the bureaucracy to take her GED and get into a (any) college. In the evenings we'd all talk about those types of struggles and how to solve the problems. We encouraged our kid to spend a lot of time with her. Those weeks made a gargantuan impression on our then 13-year-old.
I can vouch that when you ask a teenager "What
were you thinking?!?" the answer will either be "Hunh?" or "Uh, about what?"
You can try to [-]arm[/-] prepare yourself by reading the comic strip "Zits"...