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Has anyone used TurboTax for this? I'm filing for the first time too and wondering if it asks for exact days or gives you some kinda calculator to figure it out.
I used TurboTax last year and it does ask for days worked in some situations, especially if you moved between states or worked in multiple states. It doesn't have a built-in calculator, it just has a field where you input the number. I ended up counting days from my calendar where I'd marked my shifts.
I went through this exact same situation last year! For my irregular retail schedule, I ended up creating a simple spreadsheet where I listed each month and estimated how many days I typically worked based on what I could remember. I looked at my bank account to see when I got paid (usually every two weeks) and worked backwards from there. Like if I got paid on the 15th and 30th, I knew I probably worked most days in the two weeks leading up to each payday. Also check if your employer has an online portal or app - mine had all my old schedules going back months that I completely forgot about! Even if you can't find exact records, the IRS accepts reasonable estimates as long as you're making a good faith effort. Don't stress too much about being off by a few days here and there.
This is such a smart approach! I never thought about using bank deposits to work backwards. I'm in a similar situation with my first filing - worked at a coffee shop with totally random hours. Do you remember roughly how accurate your estimate ended up being? I'm worried about being way off and getting in trouble with the IRS later.
Just wanted to point out something nobody's mentioned: mortgage interest and property taxes are ALREADY deductible on your personal return if you itemize deductions, even without an LLC. Setting up this complex structure won't give you any additional benefit for those specific expenses. The only potential tax advantage is writing off depreciation and renovation costs, but as others have pointed out, most renovations would be capital improvements depreciated over 27.5 years - not immediate deductions. Also, mortgage lenders almost certainly won't give you a residential mortgage rate for an LLC purchase. You'd likely need a commercial loan at 1-2% higher interest, which would immediately negate many tax benefits.
I thought the Tax Cuts & Jobs Act limited SALT deductions to $10k? If property taxes are high in OP's area, wouldn't the LLC structure help get around that limitation?
Good point about the SALT limitation! However, the LLC rental structure doesn't actually help circumvent the $10k SALT cap. Property taxes paid by the LLC would still be subject to the same limitations when they flow through to your personal return via Schedule E. The IRS specifically addressed this in guidance following the Tax Cuts and Jobs Act. The LLC rental income and expenses (including property taxes) would be reported on Schedule E, but the property tax portion would still count toward your overall SALT limitation. Some states tried to create workarounds with "passthrough entity taxes," but these are complex and don't apply to single-member LLCs anyway. So unfortunately, the LLC structure won't help you get around the $10k SALT cap - you'd still be limited to the same deduction whether you own the property personally or through an LLC.
As someone who's been through a similar analysis, I'd strongly recommend against the LLC approach for your situation. The math just doesn't work out favorably when you factor in all the additional costs and complications. Here's what you should consider instead: Since you're planning to live there as your primary residence, focus on the HELOC strategy mentioned earlier. You'll get immediate interest deductions on funds used for substantial improvements, and it's much simpler administratively. For the renovations, document everything meticulously. While you can't deduct them as a homeowner, they'll increase your cost basis when you sell, which reduces any potential capital gains. Given that you expect only modest appreciation, this could actually eliminate most or all taxable gains. Also consider timing your purchase and renovations strategically. If you're expecting higher income years during your 5-year ownership period, concentrate the major improvement projects (and corresponding HELOC interest deductions) in those years to maximize the tax benefit. The LLC structure would cost you thousands in additional fees, higher mortgage rates, lost homestead exemption, and preparation costs while providing minimal actual tax benefit. Sometimes the simplest approach is the best one.
This is excellent advice that really synthesizes all the key points from this discussion. The HELOC approach seems much more straightforward and achieves most of the same tax benefits without the legal complexity. One question about the cost basis documentation - do you need formal receipts for everything, or would bank statements and photos of the work be sufficient? I'm thinking about smaller improvements that might not have traditional invoices, like if I do some of the work myself or buy materials from multiple stores. Also, when you mention timing renovations with higher income years, are you referring to maximizing the value of the HELOC interest deduction, or is there another tax strategy I'm missing?
I think everyone's missing something here. While buying stocks/ETFs with company money doesn't create a deductible expense, there could be strategic reasons to do it anyway. My S-corp holds some investments as part of our cash management strategy. The key is understanding it won't reduce your current tax liability. Also, talk to your accountant about the Qualified Business Income deduction (Section 199A) - if your business qualifies, it can give you a deduction up to 20% of your qualified business income. Much more valuable than trying to hide money in investments.
Are there any downsides to having your S-corp hold investments? Like liability issues or complications at tax time?
There are definitely some considerations when having your S-corp hold investments. On the liability side, corporate investments generally maintain the same liability protection as other business assets, but you want to make sure the investments align with your business purpose. The bigger issues are usually at tax time. Investment income and losses flow through to your personal return, but they're treated differently than business income. Capital gains/losses have different rules and limitations than ordinary business income. Also, if your S-corp starts looking more like an investment company than an operating business, you could run into issues with the IRS questioning your business purpose. Another thing to consider is that when you eventually want to take money out, you'll need to either take distributions or sell the investments first. It can complicate your cash flow planning compared to just keeping cash available.
This is a really common question for S-corp owners! As others have mentioned, investing company cash in stocks/ETFs won't reduce your current tax liability since it's just converting one asset to another, not creating a deductible expense. However, there are some legitimate year-end tax strategies worth considering with that $75k: 1. **Accelerate business expenses**: Purchase equipment, software, or supplies you'll need in 2026 before year-end 2. **Maximize retirement contributions**: Solo 401k or SEP-IRA contributions can be substantial for S-corp owners 3. **Consider bonus depreciation**: Qualifying business assets may be eligible for immediate depreciation 4. **Prepay deductible expenses**: Insurance, rent, or professional services for early 2026 The key is making sure any purchases are ordinary and necessary business expenses, not just trying to park money somewhere. The IRS looks at the substance of transactions, so everything needs to have a legitimate business purpose. I'd strongly recommend consulting with a tax professional who can review your specific situation - the savings from proper year-end planning often far exceed the consultation cost.
This is really helpful advice! I'm curious about the bonus depreciation you mentioned - what types of business assets typically qualify for immediate depreciation? And is there a dollar limit on how much you can depreciate in one year? I've got a consulting business (also S-corp) and wondering if things like office furniture or computer equipment would qualify.
Lifehack: If you file a paper return instead of e-filing, you're much less likely to get flagged for identity verification. I haven't been asked to verify in 5 years since I switched to paper filing. Yes it takes longer initially but no verification hassles.
but paper returns take forever to process. last year it took like 4 months to get my refund when I filed by mail
Ugh, the whole identity verification process is such a nightmare! I went through this exact same thing last year. Filed early, got accepted immediately, then... nothing. Blank transcripts for weeks while I watched everyone else get their refunds. When I finally did the in-person verification, it took about 12 days for my transcript to update and then another 4 days for the actual refund to hit my account. The appointment itself was super quick - maybe 15 minutes - but the waiting afterward was brutal. One thing I learned: call your local office RIGHT when they open (usually 7 AM) to get an appointment. They release new slots each morning and they go fast. Also bring literally every piece of ID you own - I brought driver's license, passport, social security card, birth certificate, W-2s, and a utility bill. They didn't need everything but better safe than sorry! The verification system is completely broken though. How do they expect you to have a code from a letter that doesn't exist? π€¦ββοΈ Good luck with your appointment - hopefully you'll see movement soon!
Lauren Johnson
The community wisdom on identity verification seems to be: 1. It's probably legitimate, but the agent was incorrect that "everyone" has to verify 2. You might, possibly, be able to verify before receiving your letter if you speak to the right agent 3. The timeline they gave you is somewhat accurate, though perhaps a bit pessimistic 4. It may be worth trying to call again to see if a different agent gives you different options 5. Once verified, it typically takes about 9 weeks, give or take, for processing to complete In my experience, it's generally best to follow the official process, but it doesn't hurt to try calling again for more information.
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Yara Sabbagh
I'm going through something very similar right now! Filed January 28th and got the same runaround about needing ID verification. The part about "everyone eventually needing to verify" definitely sounds wrong based on what others are saying here. I've been checking my IRS online account daily and still no verification notice posted there. Did they give you a specific reason for the verification requirement, or was it just a generic "fraud prevention" explanation? I'm debating whether to call back and try to get a different agent like some people mentioned, or just wait it out. The April timeline they gave you seems excessive compared to what others have experienced.
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