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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.
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!
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.
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.
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.
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?
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.
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!
Aria Washington
I went through something similar with about $40k in back taxes from my consulting business. One thing I didn't see mentioned yet - look into penalty abatement! If this was your first time getting into tax trouble, you might qualify for First-Time Penalty Abatement which could significantly reduce what you owe. In my case, about $12k of my bill was penalties and interest. I filed for abatement using Form 843 and got most of the penalties removed. Didn't solve the whole problem but made it much more manageable. Also, definitely file your CNC request properly. If you get approved for CNC status, the 10-year statute of limitations continues to run while you're in that status. After 10 years, any remaining tax debt can expire (though there are exceptions).
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Liam O'Reilly
ā¢How complicated is the penalty abatement form? Did you need help filling it out or is it something that's pretty straightforward?
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Aria Washington
ā¢The penalty abatement form (Form 843) is actually pretty straightforward. It's just two pages, and for First-Time Penalty Abatement, you basically need to explain that you've had a good compliance history before this issue and had reasonable cause for the failure to pay. I wrote a simple letter stating I had always filed and paid on time previously, was unaware of the proper estimated tax requirements for my new business, and was now taking steps to resolve the situation. Include your contact info, the tax periods you're requesting abatement for, and why you believe you qualify. It took about 8 weeks to get approved in my case.
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Chloe Delgado
Don't forget to check if you qualify for any of the tax relief programs specific to the pandemic! If your business was affected during that time, there might be some additional options. The IRS created several taxpayer relief initiatives during COVID that some people don't know about. Also, when you file for an Offer in Compromise, the IRS uses a specific formula to determine what they'll accept. They generally want either: 1. The quick sale value of your assets, OR 2. Your monthly disposable income Ć 12 (or Ć 24 if you're paying over time) With your income and expenses, you might be able to settle for a fraction of what you owe. Don't be discouraged by the $75k figure!
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Emma Bianchi
ā¢Thanks for mentioning COVID relief options. My business was definitely affected during that time. Do you know if these programs are still available in 2025? Also, how exactly do they calculate "disposable income" for the OIC formula?
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Chloe Delgado
ā¢Many of the COVID relief options have expired, but the IRS is still processing applications submitted during the eligible periods. If your tax debt originated during the pandemic years, you might still qualify for certain penalty relief under their broader "reasonable cause" criteria. It's worth mentioning in any communications with the IRS. For calculating disposable income in an OIC, they take your gross monthly income and subtract what they call "allowable expenses." These are based on national and local standards for living expenses like housing, transportation, food, etc. The key is that they use their own standards, not your actual expenses for many categories. So if your car payment is higher than their standard transportation allowance, they'll only count the standard amount. This is where many people run into issues with OICs - the IRS might calculate your disposable income as higher than what you actually have available after paying your real bills.
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