With tabletop role-playing games (I don't play D&D), a thousand bucks and you're pretty much set up for life. You can get a huge range of beautiful dice in all sizes, a nice deck of cards, a variety of tokens and you can skip miniatures to invest in bits that are more flexible. Speaking of flexibility, a big ebook reader allows you to enjoy tons of published games and only get physical box sets or books if you really desire them as artifacts. Another big advantage is that you can spend your money slowly and just enjoy what you have first.