This is really helpful - I had no idea there was a threshold at $25k! Do you think I should try to pay $3k now to get under that limit? Would that speed things up or just complicate the application I already submitted?

Making a payment to get under the $25k threshold would definitely help speed things up. The streamlined process is much simpler and typically processes faster. It won't complicate your existing application - the IRS will just see that you've made a payment and recalculate your plan based on the new balance. Just make sure you use Direct Pay on the IRS website and select the correct tax year and reason for payment (installment agreement request). A $3k payment now would also save you quite a bit in penalties and interest over time.

Yes! The IRS2Go app is actually really good for making payments. It links directly to IRS Direct Pay and the other payment processors. I used it last year when I was in a similar situation and it worked perfectly. The interface is much easier than navigating the main IRS website.

That's a really good point I hadn't considered. Looking back at our contract, it specifically describes the fee as "payment for client acquisition services" rather than a revenue share. Would that language definitely make it a service requiring a 1099?

Based on that contract language, yes, it would most likely be considered a payment for services that requires a 1099. When the contract specifically calls it "payment for client acquisition services," the IRS would typically view that as you purchasing a service from them. If it were structured as a revenue split or commission arrangement, the contract would usually contain language about "shared revenue" or "commission splits" and might include different terms about the business relationship. The specific language in contracts really matters when determining tax reporting requirements, so you're on the right track focusing on those exact terms.

Not everyone can afford a CPA, especially small businesses just starting out. I do my own taxes to save money and questions like this are really important for DIY tax filers.

That's a fair point. I didn't mean to sound dismissive. I started doing my own taxes too but switched to a CPA once these business relationships got complicated. For DIY filers, I think the main thing is documenting everything clearly - get those W-9s from anyone you pay, track all payments meticulously, and maybe consider investing in good accounting software that flags when you need to issue 1099s. The peace of mind is worth it, even if you're handling tax filing yourself.

Wait, can you file the S Corp extension (Form 7004) electronically yourself? Or do you need a tax professional to do it? We're trying to save money where we can since our first year was so rough.

Yes, you can absolutely file the Form 7004 electronically yourself! You don't need a tax professional. You can use the IRS e-file system, or many tax software programs include the ability to e-file the extension. If you're really trying to save money, even the free versions of some tax software will let you prepare and e-file just the extension forms. Just make sure you still estimate any taxes owed properly, as the extension only gives you more time to file the paperwork, not more time to pay.

This is so important! My friend got an extension for his S Corp but didn't realize he still needed to make his quarterly payroll tax deposits on time. Ended up with some hefty penalties.

That's really helpful, thanks! Do you know if I need to include any special forms besides Schedule D for the capital loss carryover? And will Free File guide me through that process?

You'll need Form 1040 (the main tax return), Schedule D (Capital Gains and Losses), and possibly Form 8949 (Sales and Other Dispositions of Capital Assets) depending on your specific situation. These forms work together to document your capital loss carryover. Yes, the IRS Free File program will guide you through completing these forms. Most Free File software will ask about capital losses from previous years and help you properly document the carryover. Just make sure you have your previous year's tax return handy so you can accurately enter the carryover amount.

Did you end up losing the deduction completely or were you able to fix it somehow?

What exactly counts as "reasonable" interest? My parents want to charge me 1% interest on a house loan which is obviously way below market rate. Is that going to be a problem?

The IRS publishes what's called the Applicable Federal Rate (AFR) each month, which is the minimum interest rate they consider legitimate for loans. These rates are typically lower than commercial rates. For example, as of last month, the long-term AFR (for loans over 9 years) was around 3-4%. If your loan charges less than the applicable AFR, the IRS might "impute" interest, meaning they treat the loan as if it charged the minimum rate even if it doesn't.

Without proper documentation, the IRS could potentially reclassify that $200k as a gift rather than a loan, which could have significant consequences. The annual gift tax exclusion is only $17,000 per person (as of 2023), so amounts beyond that would count against your grandparents' lifetime gift/estate tax exemption.