Chocolate is one of the bigger triggers for reflux ... so you're going to have to take your chances. However, when I'm on reflux meds, I don't have any reflux problems from chocolate. I never eat large quantities of solid chocolates, but I could handle chocolate brownies and cake (made w/ cocoa powder) or stuff with chocolate chips.
They actually do make solid "milk" chocolate using soy milk -- a few of the online vegan stores carry it but I've never seen it in stores. Of course, even if the ingredients are otherwise safe, it is still very fattening and should only be consumed in very small quantities after a safe low-fat meal.
As for chocolate fake milks ... Silk's soy chocolate milk is fabulous and tastes just like real chocolate milk to me. The only way I can otherwise drink soy milk is Silk's Very Vanilla with a whole bunch of Hershey's Lite Syrup added (which is safe unless you're very sensitive to fructose). I've tried a few others and hated them, but I think I've heard good stuff about chocolate almond milk.
When I really crave chocolate, I eat a small quantity of safe chocolate chips -- like maybe 4 or 5. This usually gets me by, unless I'm PMSing, in which case a truckload of Hershey bars aren't enough.
Hope that helps. Good luck with your chocolating. 
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jen
"It's one of the most serious things that can possibly happen to one in a battle -- to get one's head cut off." -- LC
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Re: soy chocolate
