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Just curious - has anyone tried any of the YouTube channels that explain tax concepts? I've been watching "Tax Planning Strategy" channel and find their explanations way easier to understand than books sometimes.
I like "The Real Estate CPA" channel. They have awesome videos specifically about rental property tax strategies and explain things clearly without too much jargon. Their series on cost segregation studies saved me thousands on my rental properties.
Thanks for the recommendation! I'll definitely check out The Real Estate CPA channel. I agree that videos can sometimes make complex topics easier to understand than text. It helps to see someone work through examples step by step.
One thing to watch out for with tax books - make sure you're getting the most recent edition! The tax code changes every year and something that was true in 2023 might not apply for 2025 taxes. I learned this the hard way when I tried to claim a deduction that had been eliminated.
Great point! I definitely need current information. Do you have any recommendations for resources that are updated regularly?
The J.K. Lasser guides mentioned earlier are updated annually, so that's a safe bet. The "Income Tax Guide for Investors" by Michael Zhuang is also updated each year and has good real estate sections. If you want something that's constantly current, the Kiplinger Tax Letter is a subscription service that sends updates whenever tax laws change. A bit pricey but worth it if you're managing multiple properties and need to stay on top of changes.
Check with your state tax rules too! While federal deductions for unreimbursed employee expenses were eliminated, some states still allow these deductions on your state return. I live in California and was able to deduct business expenses on my state taxes even though I couldn't on federal.
Have you considered asking your employer for a raise or bonus equivalent to the cost of the trip instead of direct reimbursement? Sometimes accounting departments have strict rules about certain expense categories but more flexibility with compensation. That way you'd at least offset the cost, even if it would be taxable income.
Just want to add something nobody's mentioned yet - your withholding might seem high but have you considered your overall tax situation? Like, do you have any other income sources besides your regular job? Investment income, side hustles, etc. can change your total tax liability. Also, sometimes having slightly higher withholding can be strategic if you normally have things like capital gains or other income that isn't subject to withholding. It's a way to avoid underpayment penalties without having to make separate estimated tax payments.
No other income sources - just my regular W-2 job. No investments that generate significant income, no side hustles. That's why the high withholding seems odd to me. I don't mind getting some money back at tax time, but $4k feels excessive when I could be using that money throughout the year.
In that case, you're definitely overwithholding. With just W-2 income, you should be able to get pretty close to breaking even. The suggestions above about adjusting your W-4 are solid. One more tip - after you submit a new W-4, check your next few paychecks to make sure the changes took effect correctly. Sometimes payroll departments make mistakes implementing withholding changes. Also, if you don't want to mess with the complicated calculations, a simple approach is to just use Line 4(c) of the W-4 to specify an exact dollar amount LESS to withhold per pay period. If you're getting $4k back and have 24 pay periods, you could just put -$167 on that line to reduce each paycheck's withholding by that amount. Just make sure your payroll system allows negative numbers there.
Has anyone here used the IRS withholding calculator lately? Last time I tried it (maybe 2 years ago) it was basically unusable. Wondering if they've improved it since then?
I used it last month and it's slightly better than before but still pretty confusing. You need to have your most recent paystub AND last year's tax return handy to use it effectively. The biggest issue I had was that it doesn't handle irregular income well. I got a bonus early in the year and it threw off all the calculations. Ended up just guessing at how to adjust my W-4.
One thing to consider with charitable donations of this size is a Donor-Advised Fund (DAF). You can donate a large amount in one tax year to get the immediate deduction, but then distribute the actual gifts to charities over multiple years. This could be helpful if you want to offset this year's big gains but haven't fully decided which charities should receive what amounts. Most major investment firms (Fidelity, Vanguard, Schwab) offer DAFs and they're becoming more crypto-friendly.
Are there any minimum amounts needed to start a DAF? And do you still get the tax benefit if you don't immediately distribute the money to end charities?
Most major DAFs have minimums in the $5,000-25,000 range to open an account, which shouldn't be an issue given the size of your potential donation. Some smaller community foundations might have lower minimums if you're looking to start smaller. You absolutely get the full tax deduction in the year you contribute to the DAF, regardless of when you distribute the money to end charities. That's the main benefit! You could theoretically put in millions this year, claim the deduction now, and then take your time over many years to thoughtfully distribute the funds. The money can even be invested and grow tax-free while in the DAF. Just be aware that once money goes into a DAF, it can only come out as charitable donations - you can't take it back personally.
Has anyone here actually donated crypto directly to a charity? I'm curious about the logistics. Do they give you some kind of wallet address? Do you need a special tax form?
I donated about 3 ETH to the Red Cross last year. They have a dedicated crypto donation page with wallet addresses for different cryptocurrencies. The receipt they provided showed the USD value at the time of transfer based on market rates. I had to fill out Form 8283 for noncash charitable contributions with my tax return. My accountant said for donations over $5,000 I would have needed a qualified appraisal too, but I was under that threshold.
Thanks for sharing your experience! I didn't realize they would have dedicated wallet addresses ready to go. Did you have any issues with the Form 8283? I'm nervous about getting the valuation right since crypto prices fluctuate so much.
Bruno Simmons
Don't forget you'll need to file Form 2553 if you haven't already! That's the actual S-Corp election form. If you formed your LLC in 2023 but haven't filed this form yet, you might need to file it late with a reasonable cause statement. The IRS is sometimes lenient with first-time filers. Also, since you're not a US citizen, make sure you have an ITIN or SSN to file these forms. And depending on your country of citizenship, check if there's a tax treaty that might affect your filing requirements.
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Tasia Synder
ā¢Thanks for mentioning Form 2553! I did file that when I set up the business last year, so that part is covered. I do have an ITIN already, so that's taken care of too. Do you know if there are any state-specific forms I should be aware of too? My LLC is registered in Florida if that helps.
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Bruno Simmons
ā¢Good that you've already filed Form 2553 and have your ITIN! For Florida, you're actually in luck - Florida doesn't have a state income tax, so you won't need to file a state equivalent of the 1120-S. However, you will still need to file an annual report for your LLC with the Florida Department of State to maintain your good standing. That's done through Sunbiz.org and is separate from your tax obligations. Just make sure you're keeping good records of your business expenses versus personal expenses since that separation is even more important with an S-Corp election. The IRS tends to scrutinize single-member LLCs with S-Corp status, particularly around the reasonable salary issue.
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Aileen Rodriguez
Has anyone used TurboTax for filing S-Corp returns? I've used it for my personal taxes but not sure if it can handle the 1120-S and all the other forms for a single-member LLC with S-Corp election.
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Zane Gray
ā¢TurboTax doesn't handle Form 1120-S in their regular versions. You'd need TurboTax Business, which is their most expensive version, and even then it can be tricky for S-Corps. I've found that for S-Corps, even single-member ones, it's worth using either a dedicated tax pro or something like UltraTax or Lacerte, which are professional-grade software. The complexity with S-Corps comes with making sure you're handling the reasonable compensation requirements correctly and properly allocating between salary and distributions. Software helps, but understanding the concepts is more important.
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Aileen Rodriguez
ā¢Thanks for the info! Sounds like TurboTax Business might be overkill for my small S-Corp. I might look into those other options you mentioned or maybe just hire a tax pro for the first year until I understand the process better. It's a lot more complicated than I thought going from a simple 1040 to all these business forms!
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