Thanks for suggesting the Taxpayer Advocate Service! Have you heard if they're also dealing with major backlogs like the regular IRS departments? I'm wondering if it's worth contacting them now or waiting until I'm physically back in the US next month.

They definitely have backlogs too, but in my experience, they're still faster than waiting for the regular IRS channels to resolve issues. If you contact them now, they might be able to start your case so that by the time you're back in the US, they'll be ready to work with you more directly. One important tip: when you contact them, be very specific about the financial hardship the delay is causing. They prioritize cases partly based on the level of hardship, so if this money is important for your relocation or getting established back in the US, definitely mention that.

'Where s My" Refund has limited historical data - it usually only shows information for the current tax year and sometimes the previous one. For older refunds, especially from streamlined filings, it probably'won t show anything helpfulnow.

That's amazing! I didn't know about this policy. Do you know if it would apply to my situation since I missed 2021 and 2022? Could I get the penalties waived for just 2021 or would it not work since I missed multiple years?

The First Time Penalty Abatement typically only applies to the first tax year in which you had an issue, so in your case, it would likely only apply to 2021. It wouldn't cover 2022 because by then, you no longer had a "clean compliance history" due to the 2021 issue. The good news is that getting the penalties waived for even one year can make a significant difference. For your 2021 tax year, this could potentially save you hundreds or even over a thousand dollars depending on your original tax amount. After you file all your returns, you can call the IRS and specifically request a "First Time Abatement" for the 2021 tax year. Just make sure you've filed all your back taxes before making the request.

I used FreeTaxUSA for my previous year returns and it worked great. They charge like $15 for prior year federal returns and their interface is easy to use. You just need to make sure you're in the right tax year when you start - they have separate sections for each year.

What about the LLC protection itself? Does it actually do anything for you besides potential tax benefits? Like protecting personal assets if a trade somehow went catastrophically wrong?

The LLC provides some asset protection, but it's limited for trading activities. It mainly protects against business creditors, but since brokerages require personal guarantees, the protection for trading losses is minimal. The main benefit was being able to establish a separate business entity for tax purposes. For catastrophic trading scenarios, the LLC wouldn't protect me from losses on trades I authorized. Where it does help is separating my trading assets from personal assets for general liability purposes. I still maintain separate accounts, separate records, and never commingle personal and business funds, which strengthens both the liability protection and the tax treatment as a business.

Does making the mark-to-market election mean ALL your investments have to be treated that way? I have some long-term holdings I definitely don't want treated as ordinary income when I eventually sell.

Thank you for mentioning this! I was wondering about the documentation part. Do you recommend keeping these records for the standard 3 years like regular tax returns?

I actually recommend keeping extension documentation for at least 6 years, even though the standard recommendation for most tax records is 3 years. The reason is that extension issues can sometimes take longer to surface. Plus, these documents don't take up much space digitally. I create a tax folder for each year with subfolders for "Extension" and "Final Return" and keep all confirmation numbers, screenshots, and payment records organized there. It's saved me more than once when questions came up years later.

I switched from TurboTax to FreeTaxUSA two years ago and haven't looked back. They handle K-1s just fine in my experience (I get one from an S-Corp). Their interface for recording extension payments is actually more straightforward than TurboTax too - it's right in the "Payments" section and clearly labeled. Federal filing is free and state is only around $15. For extensions, they guide you through the same Form 4868 process.

Can a real estate agent really provide documentation that would satisfy the IRS though? I'm worried about getting audited and having to justify my numbers.

What you want is documentation showing how you arrived at a reasonable allocation, not necessarily an official appraisal. The IRS recognizes that determining exact land values isn't an exact science. A realtor can provide comparative market analyses (CMAs) of similar properties showing their land-to-building ratios, which demonstrates you used a reasonable method based on actual market data. If you're particularly concerned about audit risk, you could have the realtor write a brief letter explaining the methodology used to determine the typical ratio in your area, and keep this with your tax records. The key is being able to show you made a good faith effort to determine an accurate and reasonable allocation, rather than just making up numbers.

Is this still true with the 2025 tax year changes? I thought there was something about this rule being modified.