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Another option to consider is using a Professional Employer Organization (PEO) for your PLLC. I switched to this model last year for my S-Corp and it's been a game changer. They handle all payroll, tax filings, workers comp, and even offer benefits access at group rates that small businesses normally can't get. The big advantage is they become the "employer of record" for tax purposes, which significantly reduces your administrative burden. Costs are typically a percentage of payroll (around 2-4%) or a flat fee per employee. For a single-member S-Corp, some have special small business rates.
Doesn't using a PEO create complications with the S-Corp structure though? I heard that can cause issues with how distributions are handled versus salary.
No complications with the S-Corp structure at all. The PEO only handles the employment administration side - payroll processing, tax filings, compliance, etc. You still maintain complete control over your business operations and how you structure your compensation. Your S-Corp still exists exactly as before, and you can still take distributions separate from your salary. The PEO simply handles the W-2 employee portion of your compensation. Actually, many PEOs have specific expertise with S-Corps and can help ensure you're maintaining the proper salary-to-distribution ratio to satisfy IRS requirements while maximizing tax benefits.
Has anyone tried just paying themselves once or twice a year instead of monthly to minimize the payroll processing headache? I'm thinking of setting up my PLLC with S-Corp election but only running payroll quarterly or semi-annually to reduce the administrative work.
Quick clarification about Publication 544 that might help - this publication mainly covers sales and dispositions of assets, including capital assets. For crypto specifically, the IRS treats it as property, not currency. This means: - Every sale or exchange = taxable event - Mining = taxable as ordinary income when received - Getting paid in crypto = taxable as income at fair market value - Gifting crypto = no immediate tax implication if under annual gift limit ($15,000 in 2021) - Donating crypto = potential deduction at fair market value The 2019 reference is probably because the guidance hasn't changed substantially since then. IRS Notice 2014-21 is still their main guidance document for crypto.
What about staking rewards? Are those taxed when received or when sold?
Staking rewards are generally taxed as ordinary income when you receive them, based on their fair market value at that time. They establish your cost basis for those coins. Then, when you eventually sell those staking rewards, you'll calculate capital gains/losses based on the difference between your selling price and that initial value when received. This is similar to how mining is treated - taxed as income when received, then potentially subject to capital gains tax when eventually sold.
Does anyone know if we need to file Form 8938 for crypto holdings? My accountant said I might need to since I have over $75k in various coins but I thought that was just for foreign accounts?
Form 8938 is for "specified foreign financial assets" - the IRS hasn't definitively stated that crypto qualifies for this. Most tax pros are taking the conservative approach and including crypto if it's held on foreign exchanges and meets the threshold. Better safe than sorry with FBAR and 8938 reporting!
One thing nobody's mentioned yet - if the collectible truly has no value, have you considered just taking the loss personally before contributing it to the partnership? You could potentially claim a capital loss of $1,000 on your personal return if you can document that the collectible is worthless. That might be cleaner than contributing a worthless asset with a built-in loss that would need to be tracked through the partnership. Just a thought, since Section 704(c) allocations can get complex fast.
That's actually a really interesting approach I hadn't considered. Would I need some kind of formal appraisal to prove the collectible is worthless? Or would documentation of the scam be enough to claim the capital loss?
You don't necessarily need a formal appraisal, but you do need adequate documentation to prove worthlessness if audited. Documentation about the scam would be helpful, especially if you filed any kind of police report or complaint with consumer protection agencies. For collectibles specifically, getting a written statement from a reputable dealer in that type of collectible confirming it has minimal or no value can also be good supporting evidence. The key is showing that the loss of value is permanent, not just a temporary market fluctuation.
Wait, I'm confused about something. If you contribute property with a $1,000 basis but $0 fair market value, and later the partnership liquidates and you get nothing back for your interest, do you get to claim a $1,000 loss at that point? Or did you essentially lose the ability to claim that loss by contributing it instead of selling/disposing of it personally?
You would still eventually get the loss, but timing matters. If you contribute the property and the partnership later liquidates giving you nothing, you'd recognize a loss equal to your remaining basis in the partnership interest (which started at $1,000 but could be adjusted by partnership operations over time). The issue with contributing property with built-in loss is that Section 704(c) requires the built-in loss to be allocated to the contributing partner when the property is sold or otherwise disposed of by the partnership. But you don't lose the loss entirely - it's just a matter of when and how you get to claim it.
I went through this last year with Cook County (always late with their bills). Called the assessor's office and they told me I could look up my PIN on their website to see the assessed amount even though bills hadn't gone out yet. I paid online using that amount in December and included a printout of the assessment page with my tax documents. No issues with the IRS accepting the deduction. Most counties have the info available somehow before they mail the physical bills.
Thank you for sharing your experience! I just checked my county's website and found a property search function I didn't know about. You're right - they do have the assessed value listed even though bills haven't been mailed. Does having the assessed value mean it's officially "imposed" as someone mentioned above? I want to make sure I'm following the proper IRS guidelines.
Yes, if you can see the assessed value on the official county website, that means the tax has been "imposed" for IRS purposes. The physical bill is just a notification - the actual tax obligation is created when the assessment is finalized and recorded in the county system. Make sure to print or save a PDF of the assessment page showing the date and amount as documentation for your records. I also wrote "Property Tax Prepayment - PIN #12345" in the memo line of my check as additional documentation. The IRS never questioned my deduction.
Has anyone used the IRS's "safe harbor" rule for property tax deductions? I think if you pay based on the previous year's assessment, you should be fine claiming it in the current year since it's a reasonable estimate. My accountant said that's what we're doing this year since our county is behind too.
I believe you're confusing the safe harbor rules for estimated tax payments with property tax deductions. For property tax deductions, the tax must actually be assessed (imposed) to be deductible in the year paid. There's no safe harbor that allows you to deduct estimated property tax payments before assessment.
You're right, I misunderstood what my accountant was telling me. He was actually referring to using last year's property tax amount for estimated tax payment calculations, not for claiming the property tax deduction itself. Getting the tax terminology mixed up shows why I need an accountant in the first place lol. Thanks for the correction!
Giovanni Greco
One thing nobody has mentioned yet - after you paper file, make sure you keep proof of mailing! I was in this exact situation last year (rejection due to non-filer status) and the IRS lost my paper return TWICE. Get a certified mail receipt or similar tracking proof from whatever service you use. Also, for your state taxes, I'd recommend still filing electronically if possible. Most states have separate systems and won't reject you based on federal non-filer status. Pay what you owe to the state immediately to avoid penalties, even if your federal return is still processing.
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Fatima Al-Farsi
ā¢Can I just file my state taxes separately even if I normally do them together with my federal? I use TurboTax and I'm not sure how to separate them after I've already entered all my info for both.
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Giovanni Greco
ā¢Absolutely! Most tax software allows you to file state separately from federal. In TurboTax, after completing both returns, you can choose to e-file just the state portion. Look for filing options during the final steps - there should be checkboxes for federal and state that you can select independently. If for some reason your software doesn't allow separate filing, you can also go directly to your state's tax website. Many states offer free filing options for basic returns, and you can enter your information there independently from your federal return.
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Dylan Wright
Does anyone know how this affects my tax refund timeline? My return was rejected for the same non-filer reason, and I'm expecting about $3,000 back which I really need soon. If I have to paper file now, am I looking at months of waiting?
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Sofia Torres
ā¢Unfortunately, yes. Paper returns are taking 6-12 weeks minimum to process this year, and that's if everything goes perfectly. My brother was in your situation last year and ended up waiting almost 4 months for his refund after paper filing. The non-filer issue seems to flag returns for additional manual review too.
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