Question 1: Am I breaking a law if I use a VPN to bet in a US state that bans betting? Or is this a legal loophole?
Question 2: Is there any way I get in trouble when I pay my taxes on my earnings, or does the state not actually care, they are willing to turn their head and take their money as long as they don’t have any of the liability?
Any insight is greatly appreciated!!
(I posted this already in r/legaladvice and was prompted to also try posting here!)
The state will care a great deal, regulation of gambling is a core state power. The VPN is violating the law and terms of use of the software. When this gets discovered the platform is likely to ban you. Also, if you get an income statement (w2-g) it will be reported to your state as well and they will likely initiate an audit,
You are required to declare all income, even income from illegal activities.
You cannot use a VPN to legally bet in another state, with a legal operator. Show me proof and I’ll send you $500
I see what you did there 
Yeah, don’t send that. He’s probably going to try and report you and cash in 
I’m very serious. Post a screen grab and $500 will go to you