What's the situation with taxes? I saw many different opinions and it's always confusing.
Yes, you must taxes on winnings. It's a requirement by the IRS. For all gambling winnings in the amount of $600 or more if such winnings are at least 300 times the amount of a single wager. Also, winnings of more than $5,000 from a wagering transaction are subject to federal income tax withholding and 25% of the payoff must be withheld.
Of course you may see different requirements by state but it's better to reach the support team of your betting site. Everything is organized very well by the bookies and it's not a problem. You need just to win enough and follow the instructions.