I've been there and it's incredibly frustrating! A few things that have helped me get through IRS calls successfully: First, always test your audio immediately when they pick up - say "Hello, can you hear me clearly?" before diving into your issue. If there's any problem, ask to be transferred right away rather than struggling through a bad connection. Also, try calling from different phones/locations - I've had better luck with landlines or even switching from WiFi to cellular data. The IRS phone system is notoriously outdated, so sometimes it's just a matter of finding the right connection. Don't give up though - document each attempt and mention previous technical difficulties when you call back. The agents are usually understanding since this happens constantly with their ancient phone infrastructure!

I've dealt with this exact same frustrating situation! Here's what finally worked for me after multiple failed attempts: First, before you even explain your tax issue, do a quick audio check by saying "Can you hear me clearly?" and wait for confirmation. If there's ANY issue (static, cutting out, them asking you to repeat), immediately request a transfer - don't waste time trying to make a bad connection work. I also found that using a regular phone line instead of cell phone helped tremendously. If you only have a cell phone, try moving to different locations in your house or switching between WiFi calling and regular cellular. The IRS phone system is incredibly outdated and the agents deal with these audio problems constantly, so they're usually very patient about reconnecting you. One last tip: when you do call back, mention upfront that your previous call had technical difficulties - this helps them understand why you're calling again and they'll often try to get you connected to better equipment. Don't give up - you'll eventually get through to someone with a clear connection!

Great discussion everyone! As someone who's been wrestling with similar questions for my own small business, I wanted to add a perspective on the HSA vs FSA decision that might help others. One thing that hasn't been mentioned much is that you can actually have BOTH an HSA and a limited-purpose FSA if you structure it correctly. The limited-purpose FSA can only be used for dental and vision expenses, but it still gives you that extra $3,200 in tax-advantaged spending for those specific categories. This might be worth considering if you have significant dental work planned or wear glasses/contacts. You get the best of both worlds - the HSA for general medical expenses and long-term investment growth, plus the FSA for dental/vision with the same-year tax deduction. That said, after reading through Leo's experience with the compliance nightmare, I'm definitely leaning toward just maxing out the HSA and keeping things simple. Sometimes the administrative peace of mind is worth more than the extra tax savings, especially when you're trying to run a business at the same time. Has anyone here tried the limited-purpose FSA route, or is that just adding unnecessary complexity to an already complicated decision?

After reading through this entire thread, I'm convinced that for single-member LLCs, the HSA route is definitely the way to go if you qualify. The compliance burden for self-administered FSAs seems absolutely brutal for such a small tax benefit. I went through a similar analysis last year and ended up with an HSA through HSA Bank. The setup was incredibly straightforward - just had to verify my high-deductible health plan met the IRS requirements and I was good to go. No plan documents, no ERISA headaches, no "use it or lose it" stress. One thing I'd add to Omar's excellent points about HSAs: you can also use them for things like over-the-counter medications, menstrual products, and even certain health-related apps and devices. The qualified expense list is actually pretty comprehensive and keeps expanding. For anyone still considering the FSA route after reading Leo's compliance nightmare story, just remember that even one mistake in your plan documents or claim substantiation could trigger penalties that would wipe out years of tax savings. The risk-adjusted return on FSA self-administration just doesn't make sense for most solo operations. Stick with the HSA, invest the funds in low-cost index funds, and enjoy the simplicity. Your future self will thank you for not getting bogged down in FSA paperwork when you could be focusing on growing your business instead.

Your 82% on the first practice test is actually really encouraging! I just passed the Intuit Academy Tax Level 1 certification last month and started with very similar scores. What I found most helpful was treating each practice test as a diagnostic tool rather than just a score to beat. After each test, I'd spend time categorizing my wrong answers into themes - like "missed filing status rules" or "confused dependency qualifications" - which helped me see patterns I wouldn't have noticed otherwise. The real exam definitely emphasizes scenario-based questions where you need to apply multiple concepts together. For example, you might get a question about a divorced parent claiming a child as a dependent, which requires you to understand both dependency rules AND filing status implications simultaneously. One specific tip that made a huge difference: practice explaining tax concepts out loud as if you're teaching someone else. I found that when I could clearly articulate WHY a particular rule applies in a given situation, I was much better prepared for those complex application questions on the actual exam. Keep working through all the practice tests - you're building a solid foundation, and consistent scores in the mid-80s should definitely give you confidence to schedule the real exam. The format is very similar, just with more nuanced scenarios that test your understanding rather than just recall.

Just wanted to add my perspective as someone who recently completed the Intuit Academy Tax Level 1 certification! An 82% on your first practice test is actually quite solid - I started around 79% and was feeling pretty discouraged initially. What really helped me bridge the gap between practice tests and the actual exam was focusing on the interconnected nature of tax concepts. The real exam doesn't just test whether you know individual rules - it tests whether you can apply multiple rules together in complex scenarios. For example, you might encounter a question about a college student who works part-time, lives with their parents part of the year, and provides some of their own support. This requires understanding dependency tests, filing requirements, education credits, AND earned income rules all at once. I found that creating "decision trees" for complex topics like filing status and dependency determinations was incredibly helpful. Instead of memorizing isolated facts, I mapped out the logical flow of questions you need to ask to reach the right conclusion. Also, don't underestimate the importance of timing practice. The actual exam has that 90-minute limit, and you need to be comfortable making decisions without second-guessing yourself too much. Practice tests under timed conditions really helped me build that confidence. Keep at it - you're definitely on the right track with your methodical approach to working through all the practice tests!

Has anyone here used TurboTax for this kind of situation? I also get a car allowance from my employer AND use my car for my side business. Wondering if TurboTax handles this well or if I need to pay for a CPA this year.

I went through this exact situation last year with my consulting business and W2 job that provided a vehicle allowance. The key thing to understand is that you absolutely CAN claim depreciation on the business portion of your vehicle even while receiving a W2 stipend - they're completely separate tax situations. Here's what worked for me: I calculated my total business mileage (excluding the W2 job miles since that's covered by the stipend) and divided by total miles driven to get my business use percentage. For a $45k truck, if you use it 60% for your own business, you can depreciate 60% of the cost. Keep detailed mileage logs with dates, destinations, and business purposes. I use a simple spreadsheet that tracks: date, starting odometer, ending odometer, destination, and whether it's personal, W2 job, or my business. This documentation is crucial if you're ever audited. One more tip - consider whether your truck qualifies as a heavy vehicle (over 6,000 lbs GVWR) because you might be able to take a larger Section 179 deduction in the first year instead of spreading depreciation over several years. Just make sure your business use percentage stays above 50% to qualify.

Consider looking into Captive Insurance Companies (CICs) if you own a business or have significant business income. Under Section 831(b), you can elect to have your captive taxed only on investment income, not insurance premiums, for captives with less than $2.3M in annual premiums. This allows you to deduct legitimate business insurance premiums paid to your own captive, while the captive accumulates wealth in a tax-advantaged structure. Another often-overlooked strategy is investing in Qualified Opportunity Zone funds, which allow you to defer capital gains taxes by investing those gains into designated economically distressed communities. You get a 10% step-up in basis after 5 years, 15% after 7 years, and if held for 10+ years, any appreciation in the QOZ investment itself is tax-free. For immediate tax relief, look into Cost Segregation studies if you own any commercial real estate or rental properties. This allows you to accelerate depreciation on certain components of buildings (like flooring, lighting, landscaping) from 27.5-39 years down to 5-15 years, creating significant upfront deductions. Finally, consider establishing a Charitable Remainder Trust (CRT) if you have highly appreciated assets. You get an immediate charitable deduction, avoid capital gains tax on the sale of the appreciated assets within the trust, and can receive income payments for life while ultimately benefiting charity.

One strategy that hasn't been mentioned yet is establishing a Solo 401(k) with a profit-sharing component if you have any 1099 income. Even small amounts of consulting or freelance work can open up significant additional retirement contribution space beyond your regular employer 401(k). Also consider tax-efficient withdrawal strategies from existing accounts. At your income level, you might benefit from Roth conversions during lower-income years (if you plan any sabbaticals, career transitions, or early retirement). Converting traditional IRA funds to Roth during a year when your income dips can be incredibly valuable long-term. Don't overlook state tax planning either - depending on where you live, strategies like establishing residency in a no-tax state before retirement or timing certain income recognition around state tax rules can save substantial amounts. Finally, if you're charitably inclined, consider a Donor Advised Fund (DAF). You can make a large contribution in a high-income year to get the deduction, then distribute the funds to charities over multiple years. It's more flexible than direct charitable giving and can help with the "bunching" strategy others mentioned. The key is working with a fee-only financial advisor who specializes in tax planning, not just someone who does basic tax prep. The strategies get much more sophisticated at your income level.