KJ, maybe you should play Rob like a fly fisherman plays a brookie.

Easy does it, then reel him in.

I'd consult with a Nevada attorney (hello, Bob N.) before committing, and if you want to move forward have the attorney draft a betting agreement (if legal: may not be, then forget it) for the two of you to sign as well as escrow instructions.

Singer has no basis to insist that the IRS mail him your tax info: he should be satisfied by merely viewing it at the escrow's office.

Of course he insists on this knowing full well you wouldn't agree; maybe you should call his bluff?

You could have the agreement cover this; e.g. you will disclose the info to him AFTER the money has been paid into escrow by the two of you, and if he loses and balks at paying then the agreement says he forfeits his bet as the agreed price you charge him to view your info.

Stated differently: let the guy have it IF it guarantees you a life-changing pay day.

But of course we know this rocket will never leave the launching pad ...