This is really helpful! Did you have to wait long to get an appointment at the IRS office? I'm worried about the timing with my March 31 deadline.

When I went last year, I called on a Monday and got an appointment for Thursday that same week, but this varies dramatically by location. Some offices have a 2-3 week wait, especially during tax season. Call the appointment line (844-545-5640) ASAP to check availability in your area. If appointments are too far out, get creative - I've had colleagues who contacted their state representative's office for help expediting IRS matters when professional licenses were at stake. Their constituent services staff can sometimes work miracles with government agencies.

This is so important! Each state has different requirements for professional licenses. Some states have a "certificate of good standing" or "tax clearance" process specifically for license renewals that can be expedited.

My cousin tried claiming he was a professional gambler and got absolutely destroyed in an audit. They disallowed all his loss deductions and hit him with penalties. What kind of documentation would someone actually need to make this work?

The documentation requirements are extensive and the burden of proof is entirely on you. Your cousin's experience is unfortunately common. To successfully claim professional gambling status, you'd need: - Detailed daily logs of every bet with documentation for all sessions - Business plan showing your gambling strategy and profit approach - Records showing you treat it as a business (separate bank accounts, business methods) - Documentation of time spent (30+ hours weekly is often considered minimum) - Evidence of skill development (courses, books, analytics subscriptions) - History of consistent activity rather than sporadic betting - Profit in at least 3 of 5 consecutive years Even with all this documentation, it's still one of the most audited tax positions because the IRS is very skeptical of these claims. For most people, it's not worth the risk.

Thanks everyone for the responses. I think I get it now - basically I can't deduct gambling losses against my regular income, only against gambling winnings. Since this would be my only bet, a loss wouldn't help me tax-wise at all. I'm starting to think maybe I should reconsider this bet or at least view it purely as entertainment with no tax advantages. Might look into other ways to use that $3000 that could have better tax treatment if things don't go as planned.

Wouldn't tax-loss harvesting just create more capital losses though? I'm already trying to use up my existing losses, not create more. Or am I misunderstanding something?

You're right, I should have been more clear. Tax-loss harvesting would indeed create more capital losses, which wouldn't help your current situation where you're trying to use up existing losses. I was thinking more long-term about tax efficiency once you've used up your carryover. For your current situation, you'd want to focus on generating capital gains. Consider looking at appreciated positions you might have in other accounts that you could sell to realize gains that would be offset by your losses. Or as others suggested, investing in assets likely to appreciate that you could sell later this year for short-term gains.

Zero coupon bonds are a bit more complicated than that. With most zero coupon bonds, including Treasury STRIPS, the built-in interest (the difference between what you pay and face value) is actually taxed as interest income each year as it accrues, even though you don't receive the cash until maturity. This is called "phantom income." Municipal zero coupon bonds are generally exempt from federal income tax, so they wouldn't generate taxable income or gains that you could offset with your capital losses.

I second this. My ex-roommate stole my W-2 from our mailbox and filed with my info. The IRS agent I spoke with said a surprising number of tax identity theft cases are people you know, not random hackers.

What about hybrid workers who split time between US and international locations? We have several people who work 3 months abroad, 9 months in the US. How would you calculate that?

For hybrid workers splitting time between US and international locations, you'd need to track their time and allocate accordingly. For your example of someone working 3 months abroad and 9 months in the US, you'd allocate 25% of their R&D salary to the 15-year amortization schedule (foreign) and 75% to the 5-year schedule (domestic). Documentation is absolutely critical here. Make sure you have systems tracking where work is performed, not just where the employee's home base is. Some companies use IP address logging or formal documentation of work locations to support their allocations in case of audit.

We use TaxMatrix Pro which has a decent R&D module. It's not perfect but it lets you set up different amortization schedules and track them year over year. The reporting is decent for tax time too.