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Has anyone had issues with backdoor Roth conversions being flagged when using TurboTax? I did mine through TurboTax last year and I'm wondering if there's something in their software that doesn't properly code these transactions.
I've used TurboTax for backdoor Roth conversions for 3 years with no issues. The key is to make sure you enter the 1099-R information correctly and then answer all the questions about IRA contributions/conversions properly. The software should generate the 8606 correctly if you input everything right. Double-check that it's showing zero taxable amount on the conversion if you had no existing IRA balances.
This is unfortunately becoming a very common issue with backdoor Roth conversions. The IRS automated systems flag these transactions because they see a traditional IRA distribution without immediately recognizing the corresponding Roth conversion, especially when the 1099-R uses code "2" instead of "J". Your documentation sounds correct - Form 8606 showing the nondeductible contributions and conversions is exactly what you need. The key is presenting a clear paper trail to the IRS examiner. I'd recommend creating a simple chronological summary showing: 1. Date of traditional IRA contributions 2. Date of Roth conversions 3. Reference to your 8606 forms showing basis 4. Your 5498s confirming the transactions Include a brief explanation that these were nondeductible traditional IRA contributions that were immediately converted to Roth IRAs, which is a legitimate tax strategy. Don't get bogged down in technical details - just show them the money trail clearly. Most of these audits get resolved quickly once a human examiner reviews the complete documentation. The computer systems that initially flagged your return simply couldn't piece together the full transaction from the individual forms.
I'm going through the exact same thing! Had N/A for almost 2 months and just got the 570 code this week. From what I've researched, it usually means they're doing some kind of review but at least our returns are finally being processed. Trying to stay patient but it's so hard when you're counting on that refund š
I might have a different perspective than others here. I explored the multi-entity structure with IP holdco for my software business ($600K revenue) and ultimately decided AGAINST it. The annual compliance costs and complexity weren't worth the tax savings for me. Instead, I focused on maximizing other tax strategies like R&D tax credits, which gave me about $47K in tax savings last year with much less overhead. Sometimes simpler is better, especially at our size. Once I hit $2M+ in revenue, I'll reconsider the more complex structure.
Did you use a particular service to help with the R&D tax credits? I've heard they're available for software development but wasn't sure if my company would qualify.
As someone who's been through this exact decision process, I'd suggest starting with a comprehensive analysis of your specific situation before jumping into any complex structure. At $750K revenue, you're right at the threshold where it could make sense, but the devil is really in the details. A few key questions to consider: What's your current effective tax rate? How much of your revenue comes from IP licensing vs. direct software sales? Are you planning significant growth in the next 2-3 years? The answers will heavily influence whether the complexity is worth it. For what it's worth, I started with a simpler structure (single LLC with good tax elections) and gradually added complexity as my business grew. Sometimes it's better to implement these changes in phases rather than trying to build the perfect structure from day one. You can always restructure later when the tax savings clearly justify the additional overhead. Also worth noting - make sure you have a solid business reason for the structure beyond just tax savings. The IRS looks much more favorably on arrangements that have legitimate business purposes like asset protection, operational efficiency, or risk management.
This is really solid advice about taking a phased approach. I'm curious though - when you say you started with a "single LLC with good tax elections," what specific elections are you referring to? S-Corp election? And at what revenue point did you decide it was time to add the additional entity complexity? I'm at around $650K revenue myself and trying to figure out if I should wait another year or two before implementing a more complex structure. The administrative burden is definitely my biggest concern right now.
Quick question - does anyone know if leasing avoids this whole tax credit problem? I've heard that with leases, the leasing company can take the tax credit and pass the savings on to you in the form of a lower monthly payment, regardless of your tax situation. Is that true for 2024?
You're absolutely right about leasing! When you lease an EV, the leasing company (technically the owner of the vehicle) claims the tax credit and can pass those savings to you through reduced lease payments. This approach works regardless of your personal tax liability. Most major manufacturers, including Tesla, are already factoring the $7,500 credit into their lease calculations for 2024. This is why you might see advertised lease deals that seem surprisingly affordable compared to purchase prices. The key advantage is that you get the benefit immediately in the form of lower monthly payments without having to wait for point-of-sale implementation or tax filing season. However, remember that with a lease, you don't own the vehicle at the end unless you choose to buy it out.
I was in exactly your situation a few weeks ago - AGI around $60k and stressed about whether to wait for Tesla's point-of-sale option or just buy now. Here's what I learned after doing a ton of research: With your $65k AGI, you'll almost certainly have enough tax liability to use the full $7,500 credit when you file your 2024 taxes. The standard deduction for 2024 is $14,600 (assuming you're single), so your taxable income would be around $50,400. The tax on that income will definitely exceed $7,500, so you won't lose any of the credit by taking it on your return instead of at point of sale. The real question is cash flow - can you afford the extra $7,500 upfront and wait until next tax season to get it back? If so, I'd say go ahead and buy now. Tesla's pricing has been pretty stable lately, but there's always the risk of price increases if you wait. I ended up purchasing my Model Y in March and claiming the credit on my taxes. No regrets - the peace of mind was worth more than potentially saving a few months of waiting for a point-of-sale option that may or may not come soon.
Dmitry Smirnov
One thing to keep in mind - make sure you're keeping VERY detailed records of your poker/sports betting activities if you're reporting them as business income and setting up a SEP-IRA. The IRS scrutinizes gambling income closely, especially when it's used to establish retirement accounts. Daily logs of play time, tournaments entered, buy-ins, cash-outs, locations, witnesses, etc. - document everything. I learned this the hard way when I got audited in 2023 for my 2022 returns.
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ElectricDreamer
ā¢Do you have a particular system or app you recommend for tracking all this? I'm currently just using a messy spreadsheet but it's becoming unwieldy as my volume increases.
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Dmitry Smirnov
ā¢I use a combination of a dedicated poker tracking app (PokerTracker for online play) and a custom spreadsheet for live games. For sports betting, I use Action Network to track all my bets. The key is consistency and detail. Each day I record: date, location, game type, buy-in amount, cash-out amount, hours played, and any relevant notes. For tournaments, I track the specific tournament name/ID, buy-in, re-buys, and final position/payout. I also keep all physical receipts from casinos and screenshots of online cashouts. This level of documentation saved me during my audit.
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AstroAdventurer
Just want to add another perspective here - I went through this exact same situation last year when setting up my SEP-IRA with poker tournament winnings. The confusion around that gambling business question is totally understandable because the wording is misleading. What helped me was thinking about it this way: the IRS is trying to identify businesses that are in the gambling INDUSTRY (casinos, bookmakers, lottery operators) versus people who gamble professionally. You're a customer of gambling establishments, not operating one yourself. I selected "NO" on that question and had zero issues with my EIN approval or SEP-IRA setup. My CPA confirmed this was correct - the distinction is crucial for tax purposes but won't affect your ability to report poker/betting income as self-employment income on Schedule C. Just make sure you have solid documentation of your gambling activities as others have mentioned. The combination of professional gambling income + retirement account contributions does tend to get extra scrutiny, so having your records organized is essential.
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Andrew Pinnock
ā¢This is really helpful context! I'm in almost the exact same boat - trying to get my SEP-IRA set up with poker income before the deadline. The "customer vs operator" distinction you made really clarifies things for me. Quick question - when you set up your SEP-IRA, did your broker ask for any additional documentation beyond just the EIN to verify your self-employment income from gambling? I'm worried they might give me pushback since it's not traditional business income.
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