
IRS
CommunityGovernment Services


Ask the community...
I'm in the process of setting up a PLLC and planning to elect S-Corp status to cut down on those self-employment taxes and get my business operations more streamlined. I've got some background with partnership stuff from before (worked with K-1 forms and 1065s), but this time I'm going solo with this venture. Here's what's bugging me - in my previous business partnership, we spent a ridiculous amount on payroll expenses, and I really want to avoid that headache this time around. Since I'll be the only employee, is there any realistic way I can handle the payroll myself? Or would trying to DIY it mean I'd need to become some kind of tax code expert (definitely NOT my strength) or create more work than it's worth just to save some money? I know I can't escape paying FICA and unemployment taxes - that's just part of the deal. But I'm specifically trying to avoid those crazy payroll processing fees and all the quarterly report nonsense. Anyone have experience with this or know if there's a way to not get totally gouged on these administrative costs for a one-person S-Corp?
I've been trying to figure out how crypto trading works for tax purposes and I'm confused after reading Publication 544. Got a few questions that are driving me crazy: 1. When I buy crypto and then sell it later, is that considered "disposing" of it according to IRS rules? Publication 544 talks about disposals but I'm not sure if regular trading counts. 2. I was looking through my 2020 Schedule 1 form and couldn't find anything specifically about virtual currency. Am I missing something or was it not on there? 3. Why does Publication 544 keep referencing 2019 stuff? Is that still applicable for my current situation? 4. For my 2021 taxes (which I'm already worrying about), will I need to fill out Schedule 1 for all my crypto trades? I did a bunch of trading on Coinbase and I'm not sure how to report it all. Really appreciate any help. This tax stuff makes my head spin!
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.
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!
My property taxes always exceed the $10K SALT limit. I don't have an escrow account, so I handle the tax payments on my own schedule. Every December, I make sure to pay my property taxes so I can max out the $10,000 deduction on that year's return. This helps me avoid accidentally missing out on the tax benefit. But this year, my county is extremely behind on sending out the tax bills. We're already deep into December, and still nothing in the mail! I'm getting worried that I won't receive my property tax bill before year-end. If I don't get it by December 31st, can I still estimate the amount (it'll probably be around $13,500 based on last year's bill plus an expected increase) and pay it anyway to claim the deduction for 2023? Would the IRS accept this even without an official bill in hand? Or am I out of luck for claiming it on this year's taxes? I really don't want to lose out on that deduction since it's substantial. Any advice would be appreciated!
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!
Title: Need advice on W2 Mate vs alternatives for creating 50+ 1099s from spreadsheet data - company wants me to use outdated software 1 I've got this small client who hired me to help with their tax prep, and now they need me to generate like 50+ 1099 forms for all their contractors. I already have all the contractor data organized in a spreadsheet with names, addresses, TINs, and payment amounts for the year. The company specifically asked me to use W2 Mate to generate these forms, but I checked it out and honestly it looks pretty outdated and they want $249 for the license which seems steep for something I'd only use once or twice. Has anyone worked with W2 Mate before? Is it worth the investment or is there a better alternative out there for batch creating 1099s from spreadsheet data? I'm not looking to spend a fortune on this since it's a one-time project, but I need something reliable that can handle this volume without me having to manually enter each contractor. Any suggestions would be super appreciated!
22 If you're tech savvy at all, check out the IRS's free Filing Information Returns Electronically (FIRE) system. There's a bit of a learning curve, but it's completely free for e-filing your 1099s directly with the IRS. The catch is you need to use their specific format for the data file. I wrote a simple Python script that converts my Excel data to their required format. Saved my company thousands in filing fees over the years.
17 Have you run into any issues with the FIRE system rejecting files? I tried it once and got frustrated with all the format requirements and ended up just paying a service.
22 The FIRE system can be finicky about formatting, for sure. The most common rejection issues I've encountered were with TIN/name mismatches and control sequence errors in the file. My advice is to run the file through their test system first before submitting - that catches most formatting problems. Once you get a clean template working, you can reuse it year after year. The learning curve is steep but worth it if you're doing this regularly and want to avoid service fees.
2 Has anyone tried the 1099 service offered through Microsoft's Excel? I heard they added a built-in feature for small businesses that lets you generate forms directly from spreadsheet data.
14 I used the Excel 1099 service last year and it was decent for a small number of forms (I did about 25). The integration is pretty seamless if you're already using Excel. It's not the cheapest option though - I think I paid around $3.50 per form plus e-filing fees. And it doesn't handle state-specific forms, so I still had to do those separately. Might be worth looking at if you're only doing federal 1099-NECs and already have everything in Excel format.
I just realized something concerning on my taxes and need some help figuring this out. In 2023 I had $4800 withheld pretax from my paychecks for a dependent care FSA that went to my kids' daycare expenses. I'm now doing my taxes and noticed that when I entered my W-2 information in the tax software, it appears the amount in Box 10 (Dependent Care Benefits) is being added as earned income on Form 2441. I'm really confused because I've used medical FSA for years and never had to report those separately before. What's the difference between medical FSA and dependent care FSA? This is my first time using the dependent care option and I'm shocked at the impact - it's increasing my federal and state tax liability by around $2100! Is this normal? Am I missing something here? I thought the whole point of FSA was to save on taxes, not end up paying more.
Another thing to keep in mind with dependent care FSA - you need to use all the money by the deadline or you lose it (unlike HSA which rolls over). I learned this the hard way last year when I put too much in and couldn't use $700 before the deadline. Some employers offer a grace period of a few months after the year ends, but not all do. Make sure you check your plan rules!
Does anyone know if you can use dependent care FSA for summer camp? My kids are school age but need supervision during summer months. Would that qualify as a dependent care expense?
Yes, summer day camps generally qualify as eligible dependent care expenses for FSA purposes! This includes general day camps, as well as specialized camps focusing on sports, arts, or academics. The key requirement is that the camp enables you to work or look for work. Overnight camps do NOT qualify though, as they're considered primarily for entertainment rather than care. Also, kindergarten and higher education costs aren't eligible, as they're considered educational rather than care expenses.
Here's a simple way to think about dependent care FSA vs medical FSA: Medical FSA: Money comes out pre-tax, you spend it on medical expenses, never shows up on your tax return again. Simple! Dependent care FSA: Money comes out pre-tax, BUT the government also offers dependent care tax credits. Form 2441 makes sure you don't double dip by adding the FSA back to your income and then calculating if the credit would've been better. It's basically a "which is better" calculation.
Ella Thompson
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.
0 coins
JacksonHarris
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.
0 coins
Ella Thompson
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.
0 coins
Jeremiah Brown
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.
0 coins
Royal_GM_Mark
You technically can do this, but you need to be careful. The IRS expects regular, reasonable compensation for services performed. Running payroll just once or twice a year with large amounts can raise red flags, especially if you're taking distributions throughout the year.
0 coins