Don't forget to make quarterly estimated tax payments for next year! This is a big shock to a lot of self-employed people who are used to W-2 jobs where taxes are withheld automatically. If you don't make these quarterly payments, you'll not only face a big bill next April but might also get hit with underpayment penalties. They're due April 15, June 15, September 15, and January 15 (of the following year).

This thread has been super helpful! I'm also self-employed and had a similar panic attack when I saw my tax bill versus my taxable income. What really helped me understand it was breaking down the math: Let's say you had $25,000 in net self-employment income (after business expenses). Your self-employment tax would be roughly $3,533 (15.3% of $23,085 after the 0.9235 adjustment). Then you get to deduct half of that ($1,767) when calculating your income tax, plus your standard deduction ($14,600 for single filers), which gets you to that low taxable income of $1,347. So you're paying $3,533 in SE tax + maybe $135 in income tax = around $3,668 total. The good news is you can deduct business expenses to lower that SE tax base, and there are strategies like a SEP-IRA that can help reduce your overall tax burden as a self-employed person. It's definitely a rude awakening coming from W-2 employment, but once you understand the system you can plan better for next year!

I went through this exact same situation with my small consulting business last year! The unemployment office really just wants to see that you're being transparent about your business income (or lack thereof). What worked for me was creating a very simple one-page document with these sections: **Business Information:** Your LLC name, your name, ownership percentage, time period **Revenue:** All money received from sales ($980 in your case) **Expenses:** Break these down by category: - Initial equipment investment: $3,200 - Cost of goods sold (inventory): $600 (4 months × $150) - Transportation/mileage for restocking - Any permits, licenses, or other startup costs **Net Loss:** Show the clear loss you're operating at The unemployment representative I spoke with said they see these all the time and they're really just checking that you're not hiding significant income. Since you're clearly operating at a loss, this should actually help demonstrate that your business isn't affecting your benefit eligibility. Keep it simple, honest, and well-organized - that's all they need!

I actually just went through this process myself with my small handmade jewelry business! The unemployment office was really understanding - they just needed to see that I wasn't hiding significant income while collecting benefits. Here's what I learned: Keep your P&L super straightforward. List your total sales revenue at the top, then break down expenses into clear categories (equipment, supplies, materials, etc.). For your vending machine, that $3,200 equipment cost definitely shows you're invested in the business but not profiting yet. One tip that helped me: Include a brief note at the bottom explaining the nature of your business and that you're still in the startup phase. Something like "Specialty vending machine business launched 4 months ago, currently reinvesting all revenue into inventory and equipment." This context helps them understand why you're showing a loss. Also, don't stress about making it look super professional - mine was literally a basic Word document with clear headings and they accepted it without question. The key is being transparent and organized, not fancy formatting. Your situation actually demonstrates exactly what they want to see - someone being honest about a side business that isn't generating significant income yet.

One thing I learned the hard way - be super careful about claiming too much of your house as rental property if you ever want to claim the capital gains exclusion when selling! If you claim 60% as rental, you might only be able to exclude 40% of your gains from capital gains taxes when you sell. Also, make sure you're tracking the dates that rooms are actually rented vs. vacant. If a room sits empty for a few months while you're looking for a tenant, the expenses during that time are still deductible as long as the room is being actively marketed for rent.

Great question about the capital gains exclusion! You're right to think about maximizing deductions, but it's all about timing and your long-term plans. If you're planning to sell within a few years, you might want to be more conservative with your rental percentage claims. But if you're planning to keep the property long-term, maximizing current deductions usually makes more sense. The key is that you can qualify for the capital gains exclusion on your primary residence portion as long as you've lived in the home as your main residence for at least 2 of the last 5 years before selling. So if you're claiming 60% rental use, you'd potentially pay capital gains on 60% of your profit, but exclude up to $250k (or $500k if married) of gains on the 40% personal use portion. Run the numbers both ways - sometimes the annual tax savings from higher rental deductions outweigh the future capital gains hit, especially if you're in a high tax bracket now. A good tax professional can help you model different scenarios based on your specific situation and timeline.

I ran into this exact problem with FreetaxUSA last month! The solution was actually in a totally unexpected place. Go to the "Federal" menu, then "Deductions and Credits," then "Adjustments." There should be a section called "IRA Contributions." In that section, there's a question about "you or your spouse being covered by a retirement plan" that affects both of your calculations. If that doesn't work, there's a workaround: enter a non-deductible IRA contribution instead. Since your wife's contributions were just for rollover purposes, they should be non-deductible anyway. You'll need to fill out Form 8606 for non-deductible contributions, but that might actually be the correct approach for your situation.

I had a very similar issue with FreetaxUSA last year! The problem is that the software sometimes doesn't properly link the retirement plan coverage between spouses when calculating IRA deductions. Here's what worked for me: Go to the "Personal Info" section first and make sure your filing status is correctly set to "Married Filing Jointly." Then, in the "Income" section, look for "Retirement Plans" and make sure you've indicated that YOU are covered by an employer plan. The key step I was missing was in the IRA contribution section itself - there should be a question that asks something like "Is your spouse covered by a retirement plan at work?" Even though you already indicated your own coverage, the software needs this information entered separately for the spouse's IRA calculations. If you still can't find it, try starting the IRA section completely over. Delete any IRA entries you've made, then re-enter them step by step. The software should ask about both your coverage AND your spouse's coverage during the interview process. Sometimes the questions get skipped if you jump around between sections too much.

Is it possible theres legit extra work for your K-1s that would justify additional fees? Like if you have complex allocations or multiple classes of stock or something? Just playing devils advocate here

This is definitely not standard practice and you're absolutely right to question it. I've been through this exact situation with my S-Corp and it's frustrating when accountants try to unbundle services that should naturally go together. The Form 1120S is essentially meaningless without the accompanying K-1s - it's like preparing half a tax return. The whole point of S-Corp taxation is the pass-through treatment, which requires the K-1s to properly allocate income, deductions, and credits to shareholders. Your accountant already has all the information needed to prepare the K-1s from completing the 1120S. I'd suggest having a direct conversation with your accountant about why they consider this a separate service. If they can't provide a compelling reason (like unusually complex allocations), you might want to shop around. Most reputable tax professionals include K-1 preparation as part of their S-Corp package because they understand it's a required component, not an optional add-on. Don't let them nickel and dime you on what should be standard service. Your car analogy is spot-on.