I know the internet is not always the best place to ask for tax advice, but I am trying to plan ahead for this coming year. I plan on having several w2gs this year. It is my understanding that if my w2gs exceed the standard deduction (24k) married filing jointly), that I can itemize deductions and thereby write off losses to offset wins. What if my w2gs exceed my salary at work (if I keep my job entire year, approaching borderline leaving)? If they exceed my job income do I then file (have to?) as a professional gambler? What should I be tracking as of January? I am tracking daily wins and losses. A daily log with all machines played would be crazy, I play in about 7 or 8 properties a day at about 30+ machines a day. And casinos will not give out your "detail history" just a won/loss statement.

Also the wife makes a good salary (over 60k) would it ever be better for me to file separately from her?

If this requires a professionals help for the first year that I will be showing this much gambling income, Are there any recommendations of where to go in Vegas? in Vegas, I am sure many tax professionals are familiar with gambling income.