Taxes

How much can I cash out in chips from a table game at the cashiers cage before it is reported to the IRS? And, how do I offset my buy in from my winnings?

At $10,000.01 a CTR is filed by the casino for daily cash transactions ($10K+ of buy-ins versus $10K+ of cash-outs) and that may or may not get to a relevant place in the IRS (it's a black hole resembling a circular file), but it sticks around for several years. There's no tax form associated with cashing out that much, like you'd see with a $1200+ slot jackpot. You can't offset your buy-ins from your winnings except by taking a cashiers check from the casino for the winnings, preferably over $10K minus your buy-in.

Too many trips to the cages, a $1000 here, $1000 there, they add up if anyone is paying attention. I'd use the cage very sparingly throughout the day. Just color up and pocket the chips then go eat dinner before going back to the tables, don't stop at the cage unless you need a little cash for the bill.

Too many buy-ins is a problem too. Only bring nine $1,000 cash buy-ins with you unless you are using front money or lines of credit at the tables and markers.

Some people probably couldn't care less if a CTR is filed on them, it doesn't cost them anything.