If you choose to make a DVD with captions, only do it for YOUR OWN PERSONAL USE. I would NOT recommend you "give away copies" of the DVD to friends who do not own the DVD already. That will attract the attention of the Motion Pictures Association of America (MPAA). The MPAA is seriously cracking down on any copyright violations and won't care one bit if you tried to countersue about Title III violations. Good luck taking them on.
He's lucky. Had he continued to do that today, he might be screwed. The trend in MPAA / RIAA lobbying is to make that kind of copyright violation a criminal offense and that means jail time up the wazoo, instead of the current system where it's just a civil offense and you'll probably get fined, if that.