I hadn't even considered an EA! How did you find one who specializes in tech compensation? That price point sounds much more reasonable than what the CPAs are quoting.

I found mine through the National Association of Enrolled Agents website (naea.org) - they have a directory where you can search by specialty. I filtered for ones who listed "equity compensation" as a specialty. Many EAs who work with tech employees advertise their familiarity with ISOs, RSUs, ESPPs, and startup equity. Some even offer free initial consultations where you can discuss your situation before committing. I'd look for someone who has experience with both rental properties and equity compensation specifically. The sweet spot for your situation is definitely an EA who has tech industry experience but doesn't charge CPA rates.

Does FreeTaxUSA handle multi-state returns well? I have property in one state but live in another like OP.

Wait seriously? I had no idea about Form 1096! Is that something I can just download from the IRS website? And does it need to be mailed or can I submit it electronically somehow?

Yes, Form 1096 is required when submitting paper 1099s to the IRS. It's essentially a cover sheet that summarizes all the 1099s you're submitting. You can download it from the IRS website, but it needs to be the official red-ink scannable version - a regular printout won't be accepted. For your situation, you might want to consider e-filing instead. If you e-file your 1099, you won't need the 1096 at all. There are several IRS-approved e-filing services that make the process pretty straightforward, and it's generally faster and eliminates the risk of mail delays. Plus, you get confirmation when the IRS receives your submission.

Does the contractor copy have the same deadline? Like, are you penalized separately for sending it late to the contractor versus sending it late to the IRS?

Thank you for mentioning this! There are actually some outstanding invoices from his business that I'm still trying to collect. How exactly does the "income in respect of a decedent" work? Does it go on my return or do I need to file something separate?

The income in respect of a decedent will still go on your joint 2021 return if you're filing jointly as surviving spouse. For any payments received in 2022, that income would go on your 2022 return (which you'd file as single or qualifying widow(er) depending on your situation). You don't need to file anything separate, but it's good to keep detailed records of when these payments were received. If any large amounts come in after his date of death, you might benefit from consulting with a tax professional as there can be deductions available for any estate taxes paid on that income. This gets a bit complex, but the basic rule is that the income is taxable in the year received, regardless of when it was earned.

This is excellent advice. Also, for the SNAP question - in my experience helping clients, you should definitely file jointly for 2021 since it'll likely save you on taxes. For SNAP, bring your full tax return but also prepare a simple spreadsheet showing just your income sources separate from his. Most caseworkers will appreciate the clarity.

Oh wow, I didn't even think about the self-employment tax! This is super helpful - I definitely would have made the same mistake. Do you know if FreeTaxUSA automatically calculates that when you enter 1099 income, or is it something I need to specifically look for?

Yes, FreeTaxUSA should automatically calculate and add the self-employment tax when you enter 1099-NEC or 1099-MISC income that's subject to SE tax. But it's always good to double-check that Schedule SE is included in your forms list before finalizing. The software should walk you through questions about your business expenses too, which can help reduce both your income tax and self-employment tax. Don't forget things like mileage, home office (if applicable), supplies, software subscriptions, etc. Even small deductions add up and can offset some of that SE tax hit.

Good point! FreeTaxUSA's free tier does include Schedule C for business income but might charge for state amendments. Their premium services are still wayyyyy cheaper than H&R Block though.

International Tax Review was incredibly helpful for me, especially their special reports on BEPS implementation and digital taxation. The case studies helped me connect theoretical concepts to real-world applications. Their transfer pricing analyses are particularly strong - look for their "Transfer Pricing Forum" section which has comparative country practices.

Thanks for the tip about the Transfer Pricing Forum section! I've been struggling with understanding how different countries approach the comparable uncontrolled price method differently, so that sounds perfect. I'll definitely focus on the BEPS implementation articles too - that's an area where our course materials seem a bit outdated compared to current practice.

Don't give up! I was in your position last year. Break it into manageable chunks and focus on mastering one concept before moving to the next. I created flashcards for key treaties and principles and reviewed them during my commute. Also, don't try to memorize everything - focus on understanding the principles and knowing where to look for specific rules.