I've been operating a similar dual-business setup (marketing consultancy + small e-commerce store) for about 2 years now, and I can share some real-world insights on the single S Corp approach. **What's worked well for me:** - Combined revenue of ~$95K last year saved me approximately $13,500 in self-employment taxes compared to dual sole proprietorships - Banking: I use one business checking account but set up automatic transfers to separate savings accounts for each division - makes reconciliation much easier - Bookkeeping: QuickBooks Online with location/class tracking has been a lifesaver for keeping everything organized **Unexpected challenges I encountered:** - **Inventory accounting**: If your food truck carries inventory (ingredients, supplies), this adds complexity that pure service businesses don't have. Make sure your accountant understands food service inventory methods - **Local permits**: Some cities require separate business licenses for food service vs. professional services, even under the same entity. Check your local requirements early - **Quarterly taxes**: Estimating payments gets tricky when one business is seasonal - I ended up underpaying Q1 and Q2 last year because I didn't account for the food truck's summer surge **One tip that saved me headaches**: Set up a simple monthly "management fee" transfer from your profitable months to cover the lean months. Helps with cash flow and makes the books cleaner when one division is temporarily unprofitable. The administrative savings alone make the single S Corp worth it, especially at your revenue levels. Just make sure you have a solid bookkeeping system in place from day one!

This has been such a valuable thread! I'm in a similar boat with a photography business and a small catering operation, and reading everyone's experiences has really clarified the path forward. One additional consideration I'd add - if you do go with the single S Corp route, make sure to document your business purpose broadly in your articles of incorporation. My attorney recommended language like "engaging in any lawful business activity" rather than being too specific about the types of businesses, since this gives you flexibility if either operation evolves or you want to add new revenue streams later. Also, regarding the liability concerns others mentioned about the food truck - you might want to look into forming the S Corp in a state like Delaware or Wyoming that offers stronger liability protections, even if you operate in a different state. The additional registered agent fees might be worth it for the extra legal protection, especially with food service liability exposure. The SE tax savings alone make this a no-brainer at your revenue levels. Based on your numbers, you're probably paying around $15K annually in SE taxes that you could largely eliminate with the S Corp structure. That savings easily covers any additional administrative costs and then some!

I went through a very similar situation when I got divorced two years ago. One thing that really helped me was using the IRS Tax Withholding Estimator (it's free on the IRS website) to compare different scenarios before making any changes to my W-4. For your situation with a $68,500 salary, you'll likely qualify for Head of Household status since you have your daughter living with you most of the time and you're paying more than half the household expenses. This is much better than Single status - the tax brackets are more favorable and you'll get a higher standard deduction. I'd recommend updating your W-4 sooner rather than later, even though it means less take-home pay initially. When I waited too long to make the change, I ended up owing a significant amount because my withholding was based on married rates while my actual tax liability was calculated using single/HOH rates. Regarding that extra $50 withholding - I'd suggest keeping it for now since you're already used to that amount being taken out, and it will help ensure you don't owe at tax time during this transition year. You can always adjust it later once you see how the new withholding amounts work out.

I really appreciate everyone's detailed responses here! As someone who just went through a major life change with my own divorce finalized earlier this year, I can relate to the stress of figuring out how filing status changes will affect your finances. From my experience, I'd strongly recommend updating your W-4 as soon as possible rather than waiting until January. The longer you wait, the more you risk underwithholding for 2024. Since your divorce was finalized in 2024, you'll need to file as either Single or Head of Household for your 2024 taxes (not Married Filing Jointly as one comment suggested - your marital status on December 31st determines your filing status for the entire year). With your daughter living with you most of the time, you'll likely qualify for Head of Household status, which has much better tax brackets than Single. At your income level of $68,500, this could save you several hundred dollars in taxes compared to filing as Single. Regarding the paycheck impact, yes, you'll see a reduction in take-home pay when switching from Married to Single withholding rates. However, this is actually protecting you from owing a large amount at tax time. I'd suggest keeping that extra $50 withholding for now since you're in a transition year and it's better to be safe than sorry. The IRS Tax Withholding Estimator is your best friend right now - it's free and will give you personalized recommendations based on your specific situation.

Pro tip: stop checking and turn on email notifications in your IRS account settings. Save urself the headache 👍

From my experience, WMR updates once daily (usually overnight between 3-6am EST) and transcripts typically update weekly on Fridays around the same time. But like others mentioned, the cycle code on your transcript determines your specific update day - it's the last 2 digits of that long number on your account transcript. I used to check obsessively too until I learned this schedule! Now I just check Friday mornings and save myself the stress. The waiting game is brutal but at least knowing when to actually look helps 😊

Question for anyone who understands this better than me - I've been accumulating passive losses for years but I'm considering converting one of my rentals to a primary residence for 2 years before selling to qualify for the $250k/$500k exclusion. What happens to the suspended passive losses in that scenario?

This is a great discussion on suspended passive losses! One thing I'd add that might help with planning - keep detailed records of which years your suspended losses were generated. When you eventually sell a property, the IRS requires you to track the suspended losses in chronological order (oldest first), and this becomes important if you're doing installment sales or have multiple properties. I learned this the hard way when I sold a rental property on an installment basis. The suspended losses are released proportionally with each payment received, not all at once in the year of sale. So if you're considering seller financing or installment sales as part of your exit strategy, factor in how that will affect the timing of when you can actually use those suspended losses. Also, don't forget about the Net Investment Income Tax (NIIT) implications. When your suspended passive losses become non-passive upon sale, they can help reduce your NIIT exposure if your income is above the thresholds ($200k single, $250k married filing jointly).

Has anyone considered the impact of the "More than 50% business use" requirement? My accountant warned me that if business use drops below 50% in later years after taking Section 179, you might have to recapture some deductions.

Great question about mileage tracking! The IRS doesn't require a specific form, but they do want contemporaneous records that show date, mileage, destination, and business purpose for each trip. A spreadsheet works fine as long as it's detailed and maintained regularly. I'd recommend also keeping receipts for fuel, maintenance, and repairs - these help support your business use percentage if questioned. Some people use mileage tracking apps that automatically log GPS data, which can be helpful backup documentation. One thing I learned the hard way - don't try to reconstruct mileage logs later. The IRS really values contemporaneous record-keeping, meaning you track it as you go rather than trying to piece it together at tax time. Even simple handwritten logs in a notebook kept in your truck can work if they're consistent and detailed.