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My cousin was in almost the exact same situation - 12 years of no filing as a home contractor. What eventually happened was a client listed payments to him on THEIR taxes as a business expense, which created a mismatch that triggered IRS attention. He ended up owing around $178,000 in back taxes, penalties and interest. He had to sell his vacation property and take out a second mortgage. The IRS did put him on a payment plan, but the stress caused serious health issues and contributed to his divorce. Don't let your friend wait any longer. The IRS is way more reasonable if you come forward voluntarily versus them finding you first.
Thanks for sharing that real-world example. Did your cousin face any criminal charges, or was it just the financial penalties? My friend is terrified of actually going to jail over this.
No criminal charges in his case. The IRS generally pursues criminal cases only when there's evidence of intentional fraud, hiding assets, or extremely large amounts. They're mostly interested in collecting the money. That said, he did have to deal with a revenue officer who monitored his compliance for several years, which was stressful. The biggest impact was financial - the penalties and interest nearly doubled what he would have paid if he'd filed on time. And the stress definitely took a toll on his health and marriage.
I worked for an accounting firm that specialized in tax resolution, and saw cases like this regularly. Here's what your friend should expect: 1) The IRS generally only pursues criminal charges in cases of active fraud (fake documents, hidden offshore accounts, etc.) rather than just non-filing 2) They'll typically only go back 6-7 years for assessment unless they suspect fraud 3) If he files voluntarily before being contacted by the IRS, he'll likely avoid the worst penalties 4) The initial bill will be terrifying, but an experienced tax attorney can often negotiate it down 5) Payment plans are standard and can sometimes stretch 5+ years
Can someone actually get caught up without using a lawyer or professional service? Like, are there resources to DIY this if you can't afford professional help?
Whatever path you choose, make sure you have proper E&O (Errors and Omissions) insurance before preparing a single return. One bad mistake on a high-value client can bankrupt you without it. Also, think about your client focus. Do you want to do mostly 1040s? Or focus on small businesses? Each requires different expertise and software. I found focusing on small contractors and self-employed folks to be my sweet spot - they need more help than simple W-2 filers and are willing to pay for expertise.
Any recommendations for good E&O insurance providers specifically for tax preparers? My quote from [insurance company] seemed crazy high.
Check out Insureon or NAEA's member insurance program if you're an Enrolled Agent. I've found the NAEA rates to be quite reasonable. Also look at Landy Insurance Group - they specialize in coverage for tax professionals and understand the specific risks. Make sure your policy covers representation during audits, not just errors. The difference in premiums isn't huge but the protection is significant. My premium is around $1,200/year for $1M in coverage, which is well worth the peace of mind.
Anyone considering buying or starting a tax practice needs to factor in the massive changes coming with technology. AI and automation are already changing the industry. The basic 1040 market is getting squeezed by free/cheap DIY options. The real value is in advisory services, tax planning, and helping with complex situations. If I were starting today, I'd focus on becoming an expert in specific niches (crypto taxes, real estate investors, expat taxes, etc) rather than trying to compete on volume of simple returns.
That's a really good point about specializing. I've been wondering if the traditional tax office model will even exist in 10 years with all the AI stuff happening. Do you think it's still worth buying an existing practice with all these changes coming?
Don't forget that Robinhood's 1099-Bs are notorious for having incorrect cost basis info! I got audited in 2023 because of this. Double-check all your transactions, especially for crypto if you transferred any in from other wallets. Sometimes they show $0 basis when you actually paid something for the coins elsewhere.
Is there an easy way to fix this? I transferred some ETH from Coinbase to Robinhood in 2022 and I'm worried my 1099 is showing zero cost basis for those.
You'll need to manually adjust the cost basis on Form 8949. There's a column specifically for corrections. Just enter the correct amount you originally paid and include a brief explanation code (usually "B" for basis adjustment). Keep all your receipts and transaction records though! If you get audited, you'll need to prove your actual cost. For your ETH transfers, you'll need the original purchase price from Coinbase. The annoying part is Robinhood won't know that info, so your 1099 will likely show $0 basis. That's why many crypto traders end up significantly overpaying on taxes if they don't make these adjustments.
Has anyone had issues with Robinhood's 1099-B for wash sales spanning across both crypto and stocks? I know wash sale rules technically dont apply to crypto but Robinhood seems to be applying them anyway on my forms.
Just a reminder that you can also try contacting your former employers directly! I was in a similar situation and was overthinking it. Called HR at my old job and they emailed me a copy of my W-2 within an hour. Most payroll systems can easily generate a replacement.
I tried that first actually! One of my employers went out of business completely (restaurant that closed) and the other isn't responding to any of my emails or calls. That's why I'm looking at the Form 4852 option as a last resort.
That's definitely a challenging situation! With the restaurant that closed, you're right that Form 4852 is your best option. For the non-responsive employer, sometimes reaching out through a different channel helps - like finding them on LinkedIn or contacting former coworkers who might have better contact information. Since you've made reasonable attempts to get your W-2s, you're absolutely doing the right thing by using Form 4852. Just document your attempts to contact them in case the IRS asks questions later.
Has anyone used FreeTaxUSA for filing with Form 4852? I'm having a similar issue with missing W-2s and wondering which free service handles this best.
Yes! FreeTaxUSA does support Form 4852. I used it last year when I couldn't get a W-2 from a summer job. When you enter W-2 information, there's an option that says something like "I don't have this W-2" and it walks you through creating the substitute form. It was pretty straightforward.
Chloe Martin
I'm surprised nobody has mentioned ATX. It's what I use for my small tax business, and it's much more affordable than TaxAct. Think it was around $800 for the basic package that covers all individual returns including Schedule C. The interface isn't super modern but it's functional and their support is decent. They also have a pay-per-return option if you're just starting out.
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Natasha Volkova
β’Does ATX include all the forms I'd need for basic 1040s with some small business clients? And do they offer any kind of training or is it mostly learn-as-you-go?
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Chloe Martin
β’Yes, the basic package includes everything you'll need for 1040s including all schedules (A, B, C, D, E) and common small business forms. They actually have pretty good built-in help content - when you're on a specific form, you can access relevant IRS instructions and explanations right there. They do offer some training webinars too, usually around the beginning of tax season. The learning curve isn't too steep if you already have some tax knowledge. Their customer service can help with software questions, but they won't give tax advice (no software company really does that for liability reasons).
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Diego Rojas
One thing to consider - whatever software you choose, factor in the cost of tax research resources too! I learned this the hard way. You'll inevitably get client situations where you need to look up regulations or rulings. Tax Act Pro is decent for the price, but I ended up subscribing to TheTaxBook online ($90/year) for research. Made a huge difference in my confidence level with more complex returns.
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Anastasia Sokolov
β’Absolutely agree about need for research tools! I use both TheTaxBook and sometimes CCH answers when things get complex. Do you think the online version of TheTaxBook is better than the physical books? I'm old school and like having the paper versions.
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