I had the same issue! I think Column Tax changed their free tier qualifications this year. I ended up using FreeTaxUSA instead - it was only $15 for state filing and completely free for federal with my moderately complex return.

Thanks for the suggestion! I'll check out FreeTaxUSA. Kinda annoyed at Column Tax for the bait and switch from last year, especially since I had a good experience with their actual product.

Thanks for bringing up Form 5472! I had no idea about these additional requirements. Do you know if there are any specific reporting thresholds we need to be concerned about? The initial investment might be around 30% ownership.

With 30% ownership, you'll definitely trigger the Form 5472 reporting requirements. The threshold is 25% foreign ownership of a US corporation. This form requires disclosing "reportable transactions" between the US corporation and the foreign related party, which can include dividends, loans, or services provided between them. The form is filed with your corporation's tax return, and as I mentioned, penalties are severe - starting at $25,000 per violation and increasing if the failures continue after IRS notification. Also, there's no statute of limitations if the form isn't filed, meaning the IRS can come after you years later. I'd also recommend looking into Form 8832 (Entity Classification Election) to ensure the LLC is properly classified for tax purposes based on your specific situation. Sometimes making an explicit election rather than relying on default classifications can provide more certainty in international structures.

You can't have a non-US citizen/resident as an S-Corp shareholder - it's one of the strict eligibility requirements. If your Canadian father wants to invest, you'd need to switch to a C-Corporation or find another structure. The tax implications are significant, though, as C-Corps face potential double taxation (corporate tax + dividend tax) while S-Corps have pass-through taxation. It's definitely worth consulting with a tax professional to find the optimal structure.

Thanks for pointing this out! I didn't even think about the asset limits. Her stock account is currently around $8,000, so I guess that would disqualify her from SSI right off the bat? Are there any programs that don't have such strict asset limits that she might qualify for?

Yes, with $8,000 in stocks she would be over the SSI resource limit of $2,000 for an individual. She would need to spend down those assets before she could qualify for SSI. Some programs with less restrictive asset limits include Medicare (no asset limit), Medicare Savings Programs (limits vary by state but are typically higher than SSI), and SNAP (many states have eliminated asset tests for food benefits). Also, some states have expanded Medicaid programs with higher asset limits. I'd recommend contacting your local Area Agency on Aging for a benefits checkup to see exactly what she might qualify for in your specific location with her current assets.

I claimed my dad as dependent last year while he was on Medicare and applying for Medicaid. The Medicaid application asked about his living arrangement and who provides support - they didn't care about my tax return but did ask about the support I provide. They calculated his benefits based on his income plus the value of the room and board I provide. He got approved for Medicaid but with a small spend-down amount.

Technically you can file as soon as the season opens IF you have all your documents. But employers aren't required to send W-2s until January 31st. So unless your employer sends them early, you'll need to wait. Don't file without all your documents! I made that mistake once and had to file an amendment, which was a huge pain.

Thanks for clarifying! I'll wait till I have everything then. Don't want to deal with amendments or worse, getting audited for missing information.

I filed early last year too and got my refund in 2 weeks with direct deposit. But I have a super simple return with just one W-2 and standard deduction. I think complexity matters more than when you file.

This is really helpful advice. Do you know if TurboTax can help me calculate how much I should be paying quarterly? Or should I just put aside 30% of everything I make to be safe?

TurboTax can give you estimated quarterly payment vouchers based on your previous year's income, but since your situation has changed, it might not be accurate. For simplicity, I'd recommend setting aside 30% of every payment you receive in a separate savings account dedicated to taxes. Then each quarter, calculate your actual tax obligation more precisely (or use a tax calculator online) and make your payment. Whatever is left in the account after your quarterlies can go toward retirement savings or other goals. This approach gives you a buffer and prevents nasty surprises.

This! I'm in California and they're even stricter about estimated payments than the feds. And their penalties are no joke either.