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Rajiv Kumar
One thing nobody's mentioned yet - you should look into establishing a separate entity specifically for your real estate development activities. I have a plumbing business and rental properties, and my CPA recommended setting up: 1. My original S-Corp for the plumbing business 2. An LLC taxed as a partnership for the rental properties 3. A separate LLC for property development/flips This way, there's no confusion about which expenses belong where. My plumbing business can legitimately bill my development projects at market rates for any plumbing work. For materials, I keep separate accounts and credit cards for each business to avoid commingling funds. For your specific situation, materials for your rentals will still need to be depreciated over time, but with the right entity structure and cost segregation, you can optimize your tax situation significantly. Just don't make the mistake of running everything through your landscaping business like I initially did with my plumbing company.
Does having multiple entities create more paperwork and higher accounting costs? I'm in a similar situation with my flooring business and some rental properties, but my accountant charges me per entity for tax filings.
Rajiv Kumar
ā¢Yes, having multiple entities does increase paperwork and accounting costs. I pay about $800 more annually in accounting fees and have additional state filing fees. However, the tax benefits and liability protection far outweigh these costs in my situation. The biggest advantage is clarity - there's no question about which expenses belong to which business. This makes documentation much cleaner if you ever face an audit. It also helps with planning because you can see the true profitability of each venture. My landscaping business seemed less profitable than it actually was when I was running some development costs through it incorrectly.
I've been doing exactly what you're trying to do for about 7 years now. Started with a painting company, moved into flips, and now have 11 rental units. Here's what I've learned: 1. For flips: You CANNOT deduct materials as expenses through your landscaping business. These costs are part of your "basis" in the property and offset your profit when you sell. You might need to amend previous returns if you've been doing this wrong. 2. For rentals: New construction costs are capitalized and depreciated over 27.5 years (residential). BUT - you can do a cost segregation study that lets you depreciate many components much faster (5-15 years). This can front-load deductions in the early years. 3. Entity structure: Consider having your landscaping business be a legitimate contractor for your real estate projects. Charge fair market rates, keep proper documentation, and you can move some profit that way. 4. 1031 exchanges: Look into these for your flips if you want to defer taxes and build your rental portfolio faster. Don't get discouraged! The tax rules for real estate actually favor investors once you understand them properly. My tax bill is way lower now than when I was just running my painting business.
I'm curious about your point #3 regarding having your business be a contractor for your own real estate projects. I do electrical work and have rental properties too. How exactly do you document this to make sure it passes muster with the IRS? Do you create formal contracts between your entities?
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One thing that really helps with wash sales is to use tax loss harvesting strategies that avoid triggering the rule in the first place. I learned this after making the same mistake. Instead of buying the exact same security within 30 days, you can buy something similar but not "substantially identical" - like a different company in the same sector or a related ETF that isn't too closely correlated. For example, if you sell MSFT at a loss, you could buy AAPL instead of rebuying MSFT within 30 days. You maintain tech exposure but avoid the wash sale rule.
What counts as "substantially identical" though? I've heard different things from different sources. Like if I sell an S&P 500 ETF (like SPY) at a loss, can I buy a different S&P 500 ETF (like VOO) within 30 days? They track the same index but are technically different funds.
Substantially" identical is unfortunately one of those gray areas in tax law. The IRS'hasn t provided extremely clear guidelines, which is why it can be confusing. For ETFs tracking the same index, like SPY and VOO both tracking the S&P 500, many tax professionals consider them substantially identical because they have nearly identical performance and holdings. So swapping between them would likely trigger wash salerules.
AaliyahAli
Has anyone used TurboTax to calculate wash sales? I have their Premier version which supposedly handles investments, but I'm not sure if it correctly identifies wash sales across multiple transactions.
I used TurboTax Premier last year and it did identify some wash sales when I imported my 1099-B from my broker. But I noticed it missed some wash sales that spanned December to January (across tax years). I had to manually adjust those. Make sure you're checking transactions that happened in January 2024 against any December 2023 sales at a loss.
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Jamal Harris
3 Has anyone tried using a tax professional instead of software? I found that some CPAs who specialize in nonresident taxation can handle these complex situations much better than DIY software, even if it costs more.
Jamal Harris
ā¢21 What's the typical price range for a CPA who knows about nonresident taxes? I'm worried it would be crazy expensive compared to software.
Jamal Harris
ā¢3 The cost typically ranges from $200-500 for a nonresident return with HSA components, depending on your location and the complexity of your overall tax situation. Some universities also have partnerships with local CPAs who offer discounted rates for international students. While it is more expensive than software, it can be worth it for peace of mind, especially if you have multiple complications like an HSA, investments, or multiple state filings. Many CPAs also offer free consultations where you can ask about their experience with nonresident returns before committing.
Jamal Harris
16 I tried GlacierTax last year but they couldn't handle my HSA either. I ended up using H&R Block's premium online version with "expat tax" add-on which surprisingly worked for my nonresident return with HSA, even though it's not marketed specifically for nonresidents.
Jamal Harris
ā¢11 Did you have any issues with the state return using H&R Block? I heard some tax software can do federal ok for nonresidents but mess up the state part.
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Lauren Wood
Honestly, the whole "hobby vs. business" thing with the IRS is more about whether you can deduct losses, not whether you need to file a Schedule C. The IRS definitely wants you to report ALL income, even if it's just occasional. I teach piano lessons maybe 5-6 times a month as a side thing, and my accountant said I absolutely need to file Schedule C even though I don't consider it a business either. The good news is you can deduct expenses directly related to your teaching - did you buy any supplies, use your car to get there, etc?
Ellie Lopez
ā¢But if it's a hobby and not a business, can you still deduct expenses? I thought the Tax Cuts and Jobs Act eliminated hobby expense deductions?
Lauren Wood
ā¢You're absolutely right about the Tax Cuts and Jobs Act eliminating hobby expense deductions - which is precisely why it's actually beneficial for the original poster to treat their teaching as a business activity on Schedule C rather than a hobby! When you report income on Schedule C as self-employment, you can deduct ordinary and necessary business expenses against that income. If you were to classify it as hobby income, you'd still have to report all the income but couldn't take any deductions against it at all, which would result in paying more tax.
Has anyone else noticed that TurboTax makes these simple situations way more complicated than necessary? I had a similar situation with some freelance writing income and TurboTax made me feel like I needed to register a corporation or something!
Try FreeTaxUSA instead! I switched last year and it's much more straightforward for handling these small 1099-NEC situations. It asks for the essential info without making you feel like you need an MBA to file your taxes.
Annabel Kimball
I think your tax pro might be confusing the rules for SIMPLE IRAs with Roth IRAs. With SIMPLE IRAs, there actually are some limitations when you have multiple retirement plans. But for your specific situation with a Solo 401k and Roth IRA, they're completely separate contribution limits as others have said. The Solo 401k falls under the 401k annual limits ($23,000 for 2025) and the Roth IRA has its own limit ($7,000 for 2025 if under 50). The only things that would prevent you from contributing to a Roth IRA would be: 1. Having income above the eligibility threshold (which you're nowhere near) 2. Not having enough earned income to cover your contributions 3. Being over 73 with no earned income (new RMD age
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Chris Elmeda
ā¢Isn't there also some rule about the total percentage of your income you can contribute across all retirement accounts? I thought I read somewhere that you can't put more than 25% of your income into retirement accounts total?
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Annabel Kimball
ā¢There is a percentage limit, but it only applies to the employer contribution portion of retirement plans. For a Solo 401k, you can contribute up to 25% of your net self-employment income as the "employer" contribution, on top of your "employee" contribution (the $23,000 limit). This doesn't affect Roth IRA eligibility or contribution limits at all. Your Roth IRA contribution is completely separate and only limited by the annual maximum ($7,000 for 2025 if under 50) and having enough earned income to cover it. Since your income is around $31,500, you're well within these limits and should be able to contribute to both accounts without any problem.
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Jean Claude
I wonder if your tax professional is thinking about the "overall contribution limit" which is $69,000 for 2025 across qualified plans. But that's mostly relevant for people with very high incomes who max out both employee and employer contributions. With your income level, there's no way you'd hit that limit. You should definitely be able to contribute to both your Roth Solo 401k and your Roth IRA as long as you have sufficient earned income to cover both. Just make sure you're tracking your business profit carefully, since your Solo 401k contributions can't exceed your actual business profit (after deducting the employer portion of self-employment tax).
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Charity Cohan
ā¢I've been doing my taxes wrong then! I thought the 401k limits were completely separate from IRA limits (which they are), but I didn't realize that the total contribution still had to be less than my business profit. My side hustle only makes about $15k but I've been maxing my solo 401k from it thinking I could use my W2 income to "cover" the rest of the contribution. Is that not allowed??
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