When I actually held federal taxes on most W-2gs, I had to enter all of them (few hundreds like your case). Since 2015, I only take taxes off "really" large W-2 wins. Hence, you only have to input and send in the W-2s that had tax withheld. For all other W-2s, you can aggregate the total amount and report under "other gambling" win. Most people playing high limit should have a log/diary so tallying up the total is not that labor intensive...

 

Damn I just spent two evenings inputting about 200 of these, this is helpful info for next year...

 

It's just a really good thing you're doing this early and leaving yourself plenty of time to deal with it all!

 

Shit I haven't even started figuring anything out.

That's what the extention is for, no?

 

I forced myself to stay in a couple nights this week to do them. So my liver and my wallet benefit. Win win. As a final number this little debacle is costing me an extra $400 on my Fed taxes. Have to write a check instead of getting one. But I see myself going back to playing more table games this year.

 

It is self reporting with a chance of getting audited. So better to cross all the t's and dot all the i's.

Most people in the US don't do withholding on their W2G wins, so they are not getting anything back on that but they have to report the offsetting losses so it zeroes out.

 

Yeah in the US you want to have the government withhold more out of your paycheck just to be safe, because if you don't withhold enough and you owe money, you might actually owe interest and minor penalties too. The government wants your money every quarter...

Also acts as forced savings because a lot of people don't have the financial discipline to keep money around to pay taxes annually.

Seems like the UK way is more efficient. Though in the US the tax code is used to promote certain activities like home ownership through debt, real estate investing etc...

 

Having lived in London for 16 years I can say I prefer UK tax system. I had to file both. The PAYE system is great, except for bonus money. I did have to write a couple large checks. But tax code was like reading a children's book compared to the morass that the U.S. System has become.