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Ask the community...

  • DO post questions about your issues.
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  • DO post tips & tricks to help folks.
  • DO NOT post call problems here - there is a support tab at the top for that :)

Emma Thompson

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Don't forget about business insurance! As a contractor myself, I discovered that general liability insurance, equipment insurance, and even health insurance premiums can potentially be deducted. This saved me thousands last year. For your husband specifically in construction, he might also be able to deduct: - Professional association dues - Subscriptions to trade publications - Work gloves, boots, and specialized clothing - Temporary job site rentals (like portable toilets) - Permits and inspection fees - Subcontractor payments (if he hires help) One thing I learned the hard way: keep METICULOUS records with dates, amounts, and business purpose for everything. Take photos of receipts before they fade. The IRS loves documentation from contractors.

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Malik Jackson

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What about software subscriptions? I use estimating software and a scheduling app for my contracting business. Are those deductible too?

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Emma Thompson

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Absolutely! Software subscriptions used for your business are definitely deductible business expenses. That includes estimating software, scheduling apps, accounting programs, design software - basically any digital tools you use primarily for your contracting work. I'd also recommend tracking the subscription costs separately in your bookkeeping since they're a different category from physical supplies or equipment. This makes tax time much smoother when you're categorizing all your deductions.

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Has anyone used TurboTax Self-Employed for this? I'm in a similar situation and wondering if it's worth the extra cost compared to the regular version.

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StarSurfer

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I used it last year for my freelance work. It's decent and walks you through most deductions, but I still found myself Googling a lot of specific questions about what qualifies. The biggest advantage is it helps calculate the self-employment tax automatically and carries information forward to your next year's return.

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NebulaNova

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Anyone else planning to amend previous returns in light of this Limited Partner Self Employment exemption ruling? My accountant says we should go back and amend the last three years, but I'm worried that would just trigger an audit.

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I would NOT voluntarily amend returns unless absolutely necessary. The IRS has said they're developing guidance on implementation, so jumping the gun could cause more problems than it solves. I'm holding off until there's more clarity.

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Paolo Conti

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For anyone wondering about the Limited Partner Self Employment exemption ruling, I consulted with a former IRS attorney yesterday. He believes the ruling will likely stand on appeal because it's based on a functional interpretation of the statute rather than adding new requirements. His take is that anyone who was truly a passive investor with no management role might still have grounds to exclude income from SE tax. The real targets are active participants using the LP structure primarily as a tax strategy despite material participation in the business. He suggested documenting your lack of involvement if you want to maintain the exemption - meeting minutes showing you don't participate in management decisions, time logs showing minimal hours, etc.

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Adrian Hughes

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Just want to add something important that nobody's mentioned yet - if you're filing a prior year return AND you owe money, you should file ASAP to minimize penalties and interest! The failure-to-file penalty is usually 5% of unpaid taxes for each month your return is late (up to 25%), while the failure-to-pay penalty is much smaller at 0.5% per month. Also, check if you qualify for "first-time penalty abatement" - if you haven't had any penalties in the prior 3 years, the IRS might waive your late-filing penalties. I saved over $400 this way!

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Do you know if you can request the first-time penalty abatement when you file the late return, or do you have to wait until after they assess the penalties?

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Adrian Hughes

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You typically need to wait until after the IRS assesses the penalties before requesting first-time penalty abatement. So you'd file your late return, receive a notice from the IRS about penalties, and then call them to request the abatement. When you call, specifically ask for "first-time penalty abatement" and explain that you have a clean compliance history for the previous three years. They'll check your records, and if you qualify, they can often approve it during that same call. It's definitely worth doing - the penalties can add up quickly on late returns!

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Ian Armstrong

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Dont forget that if youre getting a REFUND for your 2023 taxes, you have until April 15, 2027 to file and still get your money back!! But if you OWE money, your already accumulating penalties and interest. The IRS doesn't care about unfiled returns that owe them $0 or that they owe YOU money for.

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Eli Butler

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Are you sure about that? I thought the IRS requires you to file regardless of whether you're getting a refund or not. I've always heard not filing is illegal even if you don't owe anything.

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Paolo Marino

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To answer your original question simply: Your traditional IRA basis would be $0 because you've moved everything to the Roth through conversions. But you absolutely must file Form 8606 each year to track those nondeductible contributions and conversions. TurboTax should ask if you made contributions to an IRA. Tell it yes, specify they were nondeductible contributions to a traditional IRA, then indicate you converted to a Roth. TurboTax will generate the proper 8606 form if you answer all the questions accurately.

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Dmitry Volkov

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Thank you! That makes sense. So even though I put in $18,000 over those three years, since I converted it all, my traditional IRA basis is now $0. Does that mean if I check my traditional IRA account, it should show a $0 balance too?

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Paolo Marino

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Yes, if you converted the full contribution amount each year, your traditional IRA account balance should show $0 or close to it (maybe a few cents of interest if there was any time delay between contribution and conversion). Remember that "basis" refers to the money you've already paid tax on. Since backdoor Roth contributions start as nondeductible traditional IRA contributions (meaning you've already paid tax on that money), you don't pay tax again when converting to Roth as long as you convert quickly before any earnings accumulate and you properly document everything on Form 8606.

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Amina Bah

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Just wanted to add that if you're doing backdoor Roth conversions regularly, be careful about the pro-rata rule if you have any other traditional IRA, SEP IRA, or SIMPLE IRA accounts with pre-tax money in them. The IRS looks at all your IRA accounts together when calculating taxes on conversions.

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Oliver Becker

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This is such an important point! I messed this up one year when I had an old 401k that I had rolled into a traditional IRA. Made my backdoor Roth partially taxable because of the pro-rata rule. Definitely something to watch out for.

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Nia Davis

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I worked for a CPA firm for years, and honestly, there's massive variation in knowledge between professionals. Some CPAs focus almost exclusively on basic tax preparation and don't do much strategic planning. The Augusta Rule isn't obscure in tax planning circles, but if your CPA mainly does straightforward returns rather than proactive planning, she might not have encountered it often. The real question is how she responded after you explained it. Did she: 1. Dismiss it as not applicable or too aggressive? 2. Say she'd research it further to ensure proper application? 3. Immediately embrace it without verifying requirements? Her response tells you a lot about her approach. Option 1 suggests she might be too conservative. Option 3 might indicate she's too quick to accept strategies without proper diligence. Option 2 is the balanced approach you want.

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She mainly did option 2 - she acknowledged it could be useful and said she'd look into the details for my specific situation. She didn't dismiss it, which is good, but I'm still concerned that I had to bring it to her attention rather than her suggesting it as a potential strategy. Does that seem reasonable?

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Nia Davis

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That's actually a good response from her. Being willing to research and verify rather than dismissing or blindly accepting shows professional diligence. While ideally she would have suggested this strategy herself, the reality is that tax professionals can't possibly know every strategy for every client situation off the top of their heads. What matters more is her willingness to explore options you bring up and whether she proactively suggests other strategies during your planning sessions. If this is the only instance where you've felt her knowledge was lacking, I wouldn't worry too much. However, if you regularly find yourself educating her on tax strategies you've researched independently, it might be worth finding a CPA who specializes more specifically in small business and S-corp taxation.

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Mateo Perez

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Just to offer another perspective - I'm a small business owner (S-corp) and I've gone through 3 CPAs in 5 years. Each one had different strengths and knowledge gaps, which taught me something important: you need to be proactive about your own tax situation. The best client-CPA relationships are partnerships where both parties bring something to the table. Even the most knowledgeable CPA won't know every detail of your business or every potential strategy unless you have regular, detailed conversations. I'd recommend scheduling a dedicated tax planning meeting (not during tax season) to discuss various strategies including the Augusta Rule. Come prepared with questions about other potential deductions and strategies. A good CPA will appreciate a client who takes an active interest rather than seeing it as questioning their expertise.

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Aisha Rahman

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This is really good advice. Do you have any recommendations for resources where business owners can educate themselves on potential tax strategies? I feel like I don't know enough to even ask the right questions sometimes.

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