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Awesome, thanks again guys. I think I have a pretty decent idea of how to proceed now.

Thanks for the info guys, this is all good stuff. I will say, I'm a little surprised that the Starter Set has been recommended a couple of times. I bought the one for 4E (Red Box) and it felt very bare-bones. I don't really mean that it was lacking in Adventure/Fluff, I would expect that, but...

I'm a touch confused on where to start with 5E, and by that, I mean in what setting. A little background, I grew up exposed to D&D (My Dad played, and well let's just say he and I kind of grew up together because sometimes things happen earlier than you expect) and fantasy games in general...