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Great question about personal assistant deductions! I've been doing bookkeeping for several independent contractors in real estate, and there are a few additional deductions you might be missing. Since you mentioned driving to properties and running errands, make sure you're tracking ALL business miles - not just client meetings but trips to the post office, bank deposits, picking up supplies, etc. Many people only track the obvious trips. For your phone, if you have one line used for both business and personal, you can deduct the business percentage. But if you can get a separate business line, that's 100% deductible and often worth it for the clean record-keeping. One thing people often overlook: professional development expenses. Any courses, certifications, or training related to real estate or admin work are fully deductible. Same with professional memberships or subscriptions to industry publications. Also consider equipment depreciation if you bought a computer, printer, or other office equipment primarily for work. You can either deduct the full cost in the first year (Section 179) or depreciate it over several years. Keep tracking everything in a dedicated business account if possible - makes record-keeping so much cleaner come tax time!

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This is really helpful, especially the point about tracking ALL business miles! I've been missing a lot of those smaller trips. Quick question - for the separate business phone line, do you think it's worth getting a second phone or just adding a line to my existing plan? And when you mention professional development, would things like real estate software subscriptions (like MLS access or CRM tools) count as deductible expenses? I'm just starting out so trying to make sure I'm not missing anything obvious.

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Ethan Moore

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For the phone line, I'd recommend just adding a second line to your existing plan - it's usually much cheaper than getting a separate phone, and most carriers offer business line add-ons for $10-20/month. You can even get a Google Voice number for free if you want to keep costs down initially. And yes, absolutely! Software subscriptions like MLS access, CRM tools, scheduling apps, document management systems - all 100% deductible as business expenses. Same with things like Canva Pro for marketing materials, DocuSign subscriptions, or cloud storage if you use it for client files. Don't forget about bank fees either - if you open a business checking account (which I highly recommend), those monthly fees and transaction fees are deductible too. It really helps establish that clear separation between business and personal expenses that the IRS loves to see. Since you're just starting out, I'd suggest setting up a simple spreadsheet or using an app like Mint or YNAB to track everything by category. Makes tax prep so much easier when you're organized from day one!

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Lola Perez

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One deduction that's often overlooked for personal assistants in real estate is professional liability insurance! If you're handling sensitive client information or have access to property details, many real estate agents require their assistants to carry E&O (Errors and Omissions) insurance. This is 100% deductible as a business expense. Also, since you mentioned working from cafes - while the coffee itself isn't deductible, if you're buying food/drinks while conducting actual business (like client calls or work meetings), those can qualify as business meals at 50% deduction. Just make sure to note the business purpose on your receipt. For your car expenses, don't forget that parking fees and tolls for business trips are fully deductible on top of your mileage. And if you're using your personal vehicle regularly for work, consider tracking actual expenses (gas, maintenance, insurance percentage) vs. standard mileage rate - sometimes actual expenses work out better, especially if you drive an older, less fuel-efficient vehicle. One last tip: if your broker requires you to maintain a professional appearance for showings, while regular business attire isn't deductible, any special cleaning/dry cleaning costs for clothes worn exclusively during business activities can sometimes qualify. Keep those receipts and notes about the business purpose!

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This is such great advice! I had no idea about the E&O insurance being deductible - my broker has been pushing me to get it but I was hesitant about the cost. Knowing it's fully deductible makes it much more manageable. Quick question about the business meals at 50% - does this apply if I'm just taking work calls from a cafe, or does it need to be an actual meeting with clients or colleagues? I do a lot of phone work with clients while at coffee shops, but I'm not sure if that counts as "conducting business" for meal deduction purposes. Also really helpful point about parking and tolls! I've been tracking mileage religiously but completely forgot about all those downtown parking meters when I go to properties. That's probably another $50-100/month I've been missing.

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Lol this GILTI stuff is making my head spin! I think I kinda get it now - basically it's to stop companies from using fake royalty payments to move profits to tax havens right? But I'm still not clear on HOW MUCH tax you actually pay on this GILTI income? Is it the full corporate rate or something less?

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Jibriel Kohn

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For US corporations, the effective tax rate on GILTI is typically around 10.5% to 13.125% (after the Section 250 deduction), which is about half the regular corporate tax rate. This increases to 16.4% after 2025 when the GILTI deduction percentage changes. But remember, you can still claim foreign tax credits for up to 80% of the foreign taxes paid on that income. So if your foreign subsidiaries are already paying tax at rates close to these percentages, your additional US tax might be minimal.

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Omar Hassan

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This is such a helpful thread! I'm dealing with a similar situation where our company has IP licensing arrangements with subsidiaries in Ireland and the Netherlands. One thing I'm still confused about - does the GILTI calculation look at each foreign subsidiary separately, or does it aggregate all your CFCs together? I'm trying to figure out if having one profitable subsidiary with minimal tangible assets and another subsidiary with lots of equipment but lower profits would offset each other in the GILTI calculation, or if each entity gets evaluated independently. This could make a big difference in our tax planning strategy. Also, are there any safe harbors or de minimis thresholds where small amounts of CFC income might not trigger GILTI at all?

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Riya Sharma

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22 Has anyone used the "safe harbor" method for determining FMV at conversion? My accountant mentioned something about using the tax assessment value but I'm not sure if that's reliable in my area since assessments are pretty out of sync with market values.

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Riya Sharma

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8 Tax assessments can be problematic for establishing FMV because, as you noted, they're often not aligned with actual market values. The most reliable method is getting a formal appraisal at the time of conversion, but that's not always practical if you've already converted the property. You can also use comparable sales from around the time of conversion, but be prepared to document your methodology if questioned. Some people use the insurance replacement value, but that often includes land value which may skew your numbers. If you're working with an accountant, they might have access to historical property value data that could help establish a reasonable FMV.

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I went through this exact same situation two years ago when I converted my primary residence to a rental property. The key thing to understand is that you absolutely can deduct rental property losses, but only the portion that occurred after conversion. Here's what you need to do: Get a solid valuation of your property as of June 2023 when you converted it to rental use. This becomes your new basis for the rental property. Any decline in value that happened while you lived there is considered a personal loss and isn't deductible. Make sure you've been taking depreciation deductions during the rental period too - if you haven't, you'll still need to account for "allowed or allowable" depreciation when you calculate your final loss. Also keep detailed records of any improvements you made during the rental period, as these can be added to your basis. The IRS is pretty strict about the conversion rules, so documentation is key. If you're unsure about the fair market value at conversion, consider getting a retroactive appraisal or use comparable sales data from that time period.

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This is really helpful! I'm curious about the depreciation part you mentioned - what happens if someone forgot to take depreciation deductions during the rental period? Can you go back and amend previous returns to claim those, or do you just have to account for the "allowable" depreciation even though you didn't actually claim it? I'm worried I might be in a similar situation where I didn't maximize my deductions during the rental period.

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Emma Johnson

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Just as a heads up - my friend who runs an interior design business from home got audited last year and one of the things they specifically looked at was her home office client meal deductions. She got through it fine because she had detailed records - not just receipts but calendar entries showing client names, topics discussed, and outcomes of meetings. IRS apparently gets suspicious of home office food/drink deductions so documenting the business purpose thoroughly is key!

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Ravi Patel

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Did she have any alcohol purchases questioned specifically? That's what I'm most concerned about with my client meetings.

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Emma Johnson

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She did have some wine purchases for client meetings, and the auditor did ask about them. They were approved without issue because she had noted the specific clients, meeting purpose, and business discussions on her calendar and in her expense tracking system. The auditor was more concerned with making sure the food/drink was actually for client meetings rather than personal consumption than they were about the type of refreshments provided.

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Mei-Ling Chen

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This is all really helpful information! I've been wondering about this exact situation myself. One thing I'd add - make sure you're consistent with how you handle these deductions from year to year. If you start claiming home office client meal deductions, keep doing it the same way each tax season. Also, consider setting up a simple client meeting log where you record the date, client name, business purpose, and what refreshments were provided. This creates a paper trail that shows the business nature of these expenses. I use a basic spreadsheet that takes maybe 30 seconds to update after each client meeting, but it would be invaluable if I ever got audited. The key seems to be showing clear business purpose and keeping personal expenses completely separate. Thanks everyone for sharing your experiences - this gives me confidence to start properly tracking and deducting these legitimate business expenses!

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Great question about the tax strategy! The general rule of thumb is: 1) Get any employer match first (that's free money), 2) Max out Roth contributions if you expect higher tax rates in retirement, 3) Then max pre-tax contributions like SIMPLE IRA if you expect lower tax rates in retirement. But here's the key thing people miss - the backdoor Roth IRA contribution limit ($6,500 for 2023) is completely separate from the SIMPLE IRA limit ($15,500 for 2023, or $19,000 if 50+). You can absolutely do both in the same year without any issues. Since you're already above the income limits for direct Roth IRA contributions (hence needing the backdoor method), you're likely in a higher tax bracket now. The SIMPLE IRA gives you immediate tax savings, while the backdoor Roth gives you tax-free growth. If you can afford both, it's usually worth doing both for the diversification of having some pre-tax and some post-tax retirement savings.

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This is exactly the kind of comprehensive breakdown I was looking for! I hadn't fully appreciated that the contribution limits are completely separate - that makes the decision much clearer. The tax diversification angle is really smart too. Having both pre-tax SIMPLE IRA money (reducing current taxes) and post-tax Roth money (tax-free in retirement) gives you flexibility to manage tax brackets when you're withdrawing in retirement. Plus if tax rates go up in the future, you're partially protected with the Roth side. One follow-up question though - does the employer match on SIMPLE IRAs work the same way as 401k matches? Like dollar-for-dollar up to a certain percentage?

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Great question about SIMPLE IRA employer matches! Yes, but it works a bit differently than traditional 401k matches. With SIMPLE IRAs, employers typically do one of two things: 1) **Matching contribution**: Dollar-for-dollar match up to 3% of your salary (most common). So if you make $100k and contribute 3% ($3k), your employer contributes another $3k. 2) **Non-elective contribution**: The employer contributes 2% of your salary for ALL eligible employees, regardless of whether you contribute anything. This is less common but some employers prefer it for simplicity. The key difference from 401ks is that SIMPLE IRA matches are immediately 100% vested - no waiting period like you sometimes see with 401k plans. Also, the employer contributions count toward the overall SIMPLE IRA limits, not as separate "employer match" space like with 401ks. So if your wife's company does the 3% match, definitely contribute at least 3% to get that free money before worrying about maxing out other retirement accounts. That employer match is an immediate 100% return on investment that you can't get anywhere else!

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Alice Pierce

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This is super helpful! I didn't realize SIMPLE IRA matches were immediately 100% vested - that's actually a huge advantage over many 401k plans where you have to wait years to be fully vested. The 3% match scenario makes perfect sense for prioritizing contributions. So for someone in CosmicCaptain's wife's situation, the optimal strategy would be: contribute at least 3% to get the full employer match, then do the backdoor Roth IRA ($6,500), and then if there's still room in the budget, work toward maxing the remaining SIMPLE IRA contribution space. That way you're getting the free employer money first, the tax-free growth second, and additional tax deduction third. One thing I'm curious about - do SIMPLE IRA employer contributions also follow that 2-year rule, or is that restriction only on employee contributions?

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