The 1040 instructions for line 4a state "generally, you should enter the total amount of distributions from all your IRAs" so I think FreeTaxUSA might actually be right to add both? The exception cases in the instructions are super confusing tho.

I went through this exact scenario last year and can confirm TurboTax is handling it correctly. Only the conversion amount ($4,074) should go on line 4a, not the recharacterization amount. Here's what helped me understand it: think of a recharacterization as "undoing" the original contribution type. When you recharacterized from Roth to Traditional, it's as if you had originally contributed to the Traditional IRA. Then when you converted back to Roth, that's the only transaction that gets reported on line 4a. The statement TurboTax creates is crucial - it explains to the IRS why you have multiple 1099-R forms but only one amount on line 4a. Without it, your return would look like you're underreporting distributions. I was also worried about e-filing with the statement, but TurboTax handled it seamlessly. The IRS processed my return normally and I got my refund on schedule. Don't stress about it - you're doing it right!

Don't forget about self-employment taxes! That's the thing that surprised me most when I started reporting my side gig income. You're responsible for both halves of Social Security and Medicare taxes (around 15.3% total) on top of regular income tax. I recommend setting aside at least 25-30% of what you earn for taxes depending on your tax bracket. Also look into making quarterly estimated tax payments if your tax liability will be over $1000 for the year. Much better than getting hit with a huge bill and potential penalties at tax time.

Just wanted to add that if your total self-employment income is less than $400 for the year, you don't have to pay self-employment tax on it. You still need to report it as income for income tax purposes though. Also, if you're doing photography, make sure you're keeping track of all your equipment purchases, editing software subscriptions, props, travel to shoots, etc. Those are all legitimate business expenses that will reduce your taxable income.

Got mine in 3 weeks but I filed super early (late January

Filed mine on Feb 8th and still waiting too. The processing delays are brutal this year. At least knowing it's not just me makes me feel a bit better. Has anyone tried calling IDOR directly or is that pretty much useless?

One thing nobody's mentioned yet - if you're attending this conference primarily for your W-2 job, ask your employer about reimbursement instead of trying to deduct it! Many companies have professional development budgets that employees don't even know about. My company reimburses up to $2500/year for industry conferences and related expenses. Worth asking your manager or HR before paying out of pocket.

Great advice everyone! Just to add one more perspective - make sure you understand the "ordinary and necessary" test for business deductions. The IRS requires that expenses be both ordinary (common in your industry) and necessary (helpful for your business). For a conference in your field, this is usually pretty straightforward to meet. But document HOW the conference relates to your 1099 work specifically. Write down which sessions you attended, what you learned, and how it applies to your consulting work. This creates a clear business purpose trail. Also, if you're networking at the conference, keep notes on business contacts you made. The IRS likes to see that you're actively using the conference for legitimate business purposes, not just treating it as a vacation with some business mixed in. The fact that you're planning ahead shows you're taking this seriously - that's exactly the right approach! 👍

Make sure you understand the difference between employees and independent contractors too. If these people are legitimate independent contractors (responsible for their own work methods, use their own equipment, work for multiple clients, etc.), then the tax reporting requirements are different. The company would still need to issue 1099s for payments over $600, but wouldn't be responsible for payroll taxes. That said, from what you described - regular weekly payments that sound like wages - this sounds like employee misclassification, which is definitely something the IRS cares about.

Just want to add something about documentation that might help - even without access to official payroll records, there are ways to strengthen your case. Keep a detailed log of what you observe: dates, approximate amounts you see being handed out, which employees receive cash payments, any overheard conversations about the arrangement, etc. Also, if you have any text messages, emails, or written communications that reference the cash payment system, those could be valuable. Even seemingly innocent messages like "pick up your pay from John's office" or references to "cash bonuses" can help establish a pattern. The IRS investigators are experienced with these situations and know how to build cases from circumstantial evidence. Your firsthand observations as an employee carry significant weight, especially if you can provide specific details about the scope and duration of the scheme. One more thing - document everything you can about the working conditions of these cash-paid workers. If they're clearly employees (set schedules, using company equipment, following company procedures) rather than independent contractors, that strengthens the misclassification aspect of the case.