Oh, I didn't realize I had to pay part of the offer upfront. Is the 20% non-refundable even if they reject my offer? And how do they determine if I qualify for the Low-Income Certification?

The 20% payment is non-refundable, unfortunately, even if your offer is rejected. That's why it's so important to make sure your offer is realistic and well-documented. For Low-Income Certification, it's based on your household size and income. For 2025, if your household gross income is at or below 250% of the federal poverty guidelines, you qualify. For a single person, that's about $36,450. If you're receiving unemployment, you might qualify. Check Box 1 on Form 656 and the IRS will verify your eligibility - if approved, both the $205 application fee and the 20% initial payment are waived.

Does including a hardship letter help with OIC applications? I've heard mixed things about whether personal statements make any difference.

This is what I did! I logged into my H&R Block account from last year and found my original filing. The AGI was completely different from what I thought it was after the adjustment.

Good point about checking all possible tax software accounts! Sometimes people forget which service they used the previous year, so it's worth checking any tax preparation accounts you might have.

That $0 AGI workaround only works in specific situations - primarily for first-time filers or in years when the IRS specifically allows it. For most people who filed last year, using $0 will cause another rejection. The IRS has been inconsistent with this policy, so it's better to find your actual AGI if possible.

Do you know if this applies to sales tax collection too? I'm in TX with a single-member LLC and I'm confused about whether the disregarded status affects my sales tax obligations.

Good question about sales tax. The disregarded entity status generally doesn't affect your sales tax obligations. In Texas, you still need to collect and remit sales tax based on your LLC's activities, regardless of how it's treated for income tax purposes. Your LLC is still recognized as the legal business entity that's making the sales, so the sales tax registration and collection responsibilities belong to the LLC. Texas doesn't really care that you're disregarded for federal income tax purposes - they just care that you collect the proper sales tax on taxable transactions.

It's actually a good thing! "Disregarded entity" sounds negative but it just means the IRS is ignoring your LLC as a separate tax entity. You report business income on your personal return with Schedule C (same as a sole proprietorship). Benefits: One tax return instead of two, possible loss deductions against other income, simpler paperwork. You still get the legal liability protection of an LLC - that doesn't change!

Wow, I hadn't thought about the basis step-up issue at all. Does this mean I should be gifting cash rather than appreciated investments if I do start annual gifting? Or is there some strategy that lets you get the best of both worlds?

Yes, if you're going to gift, cash or high-basis assets are generally better from a tax perspective. You want to keep the low-basis (highly appreciated) assets in your estate to get that step-up when you pass. Another strategy some people use is life insurance. If you're worried about estate taxes but want to preserve the step-up, you can keep your appreciated assets and buy life insurance in an irrevocable life insurance trust (ILIT) to provide liquidity for any estate taxes. The insurance proceeds, if structured correctly, pass outside your estate and can be used to pay any estate tax due, allowing your heirs to keep more of your assets intact.

I disagree with your "use it or lose it" framing. While you can't recover unused annual exclusions, you still have your lifetime estate/gift tax exemption. So it's not like those opportunities to transfer tax-free are gone forever if you don't make annual gifts. Also, compounding works the same whether the money is in your account or your child's account. The real question is whether you think you'll exceed the lifetime exemption (even after it decreases), which most people won't.

Thanks for the suggestion. How long does it typically take to get help from the Taxpayer Advocate Service? Do they have the same backlog as regular IRS services?

The Taxpayer Advocate Service does have some backlog, but generally they can get to you within 1-2 weeks which is much faster than waiting for regular IRS correspondence. They prioritize cases with imminent deadlines, so if you explain you're trying to file before the deadline, they often expedite. When you contact them, be very clear that you've attempted all normal channels for obtaining your IP PIN with no success. They can often issue temporary PINs or provide alternative filing guidance.

Yes! This happened to my cousin. She filed paper without her IP PIN (after identity theft) and it took 14 months to resolve the issues it created. They froze her refund and she had to go through a whole identity verification process in person.