I can tell you the status of online gambling in Florida, having delt with the issue recently. According to the FDLE, online gambling in Florida is NOT REGULATED. The technology has far outpaced the law in this area, with the result that, although the state of FL very much wants to regulate it, there are no enforcible laws or legislation. One major problem is jurisdiction.
For example, if you live in Florida, and you make a wager from your computer using an online gambling website who's server is based off-shore in Costa Rica, where gambling is legal, you run into a jurisdiction quandry. Where is the internet located? It is everywhere at the same time. How do you solve the issue of jurisdiction. There is plenty here to stymie prosecutors.
General consensus is that Federal laws stand the best chance of regulating it, but perhaps only via indirect laws directed at banks, credit cards, etc used in transactions. It remains to be seen how effective recent laws will be... perhaps gamblers will use paypal ....