Just wanted to add some clarity on the record-keeping requirements if you do end up qualifying for any vehicle deductions through self-employment activities. The IRS is particularly strict about vehicle expense documentation, so you'll need to maintain contemporaneous records showing: 1. **Mileage logs** - Date, destination, business purpose, and odometer readings for each trip 2. **Total annual mileage** - Both business and personal use to calculate your business use percentage 3. **Actual expenses** - If you choose actual expense method over standard mileage rate, keep receipts for gas, maintenance, insurance, etc. For Section 179 specifically, remember that if your business use drops below 50% in any subsequent year, you'll have to "recapture" some of the deduction as income. This is why accurate ongoing record-keeping is crucial. I'd also suggest consulting with a tax professional before making a large vehicle purchase with the intent to claim Section 179. The interaction between W2 income and self-employment income for vehicle expenses can get complex, and the penalties for getting it wrong can be significant.

Based on all the discussion here, it sounds like your best immediate option as a W2 employee is to approach your employer about setting up an accountable plan for vehicle reimbursement, as Ava mentioned. This would give you tax-free reimbursement at the current 67 cents per mile rate without the complexity of trying to qualify for Section 179. However, if you're serious about the Section 179 deduction, you might want to consider whether any of your work activities could qualify as legitimate self-employment. For example, if you're doing networking events that could lead to consulting opportunities, or if you have any skills you could offer as independent services, you might be able to establish a legitimate side business that would qualify for Section 179. The key thing to remember is that the IRS looks at substance over form - you can't just call yourself self-employed to get tax benefits. You'd need genuine business activities with profit motive, separate from your W2 work. Given the record-keeping requirements and recapture risks that Hannah outlined, make sure any business use percentage you claim is well-documented and conservative. I'd definitely recommend consulting with a tax professional before making a major vehicle purchase, especially one where you're counting on Section 179 benefits to justify the decision.

Wait I'm confused - I thought home office deduction was part of itemizing? So if I take standard deduction I can't claim my home office for my sole proprietorship? I've been doing this wrong for years then!

This is such a common misconception! I went through the exact same confusion when I started my consulting business. The key thing to remember is that Schedule C business expenses and the standard deduction operate on completely different "levels" of your tax return. Think of it like this: Schedule C calculates your net business profit (gross income minus business expenses), and that net profit number flows to Line 3 of your Form 1040. Then, much later in the process, you decide whether to take the standard deduction or itemize your personal deductions. So yes, absolutely organize those receipts and track your business expenses! Every legitimate business expense reduces both your income tax AND your self-employment tax (which is 15.3% on net earnings). Even if your business has slowed down, those deductions are still valuable. For your accountant, provide everything you mentioned: all 1099s/W2s, organized business expenses by category, and your investment statements. Since you have a Solo 401k, make sure to include any contributions you made there too - those are also deductible regardless of whether you itemize or take the standard deduction.

Don't forget about the annual price increases!! I started with ProSeries 7 years ago and my cost has doubled since then. They get you with the low initial price but then jack it up every year knowing it's too much of a pain to switch.

For growing a practice with complex multi-state and partnership returns, I'd strongly recommend considering CCH Axcess Tax or Thomson Reuters UltraTax CS as your primary options. Both handle complex business structures exceptionally well and won't limit your growth potential. From my experience, Drake is great for straightforward returns but becomes cumbersome with multi-state allocations and complex K-1 flow-throughs. ProSeries falls into a similar category - fine for basic practice but you'll outgrow it quickly if you're targeting complex business clients. One thing to really consider is the total cost of ownership beyond just the software license. Factor in training time, support quality (as others mentioned), and the efficiency gains on complex returns. A more expensive platform that saves you 30 minutes per complex return will pay for itself quickly. Also, whatever you choose, negotiate a multi-year price lock if possible. The annual price increases can really add up over time, and having predictable costs helps with business planning. Some vendors are willing to work with you on this, especially if you're switching from a competitor.

This thread has been incredibly helpful! I'm currently dealing with a similar situation and wanted to share something I learned from my tax professional that might help others. If you're using the health insurance premium exception, make sure you understand how it interacts with any premium tax credits you might have received from the marketplace. If you received advance premium tax credits (APTC) to help pay for your marketplace plan, you can only claim the early withdrawal exception for the portion of premiums you actually paid out-of-pocket, not the total premium amount. For example, if your monthly premium was $400 but you received $200 in advance credits, you can only count the $200 you actually paid when calculating your exception amount. This caught me off guard initially because I was looking at the total premium cost on my 1095-A form rather than my actual out-of-pocket payments. Also, a heads up for anyone who had both COBRA and marketplace coverage in the same year - you'll need to track both separately since the documentation requirements are slightly different. COBRA statements are usually more straightforward, but marketplace coverage requires the 1095-A form to verify your actual premium payments versus any credits received. The good news is that both types of coverage qualify for the exception as long as you were unemployed and receiving compensation during the payment periods!

This entire discussion has been incredibly thorough and helpful! As someone who works with retirement distribution issues regularly, I want to emphasize a few key takeaways for anyone in a similar situation: First, the health insurance premium exception is one of the most misunderstood 1099-R penalty exceptions. The IRS doesn't require you to prove the specific dollars from your withdrawal went directly to premiums - you just need to show you were unemployed, receiving compensation, and paying qualifying premiums during the eligible timeframe. Second, documentation is absolutely critical. I've seen too many people try to claim this exception years later without proper records. Keep everything: unemployment notices, premium bills, payment confirmations, COBRA elections, marketplace enrollment docs, and 1095-A forms if applicable. Third, timing matters but is more flexible than people think. You can withdraw during the year you received unemployment OR the following year, and up to 60 days after returning to work. The key is that your premium payments occurred while you were eligible. Finally, don't forget about the interaction with premium tax credits that Liam mentioned - this trips up a lot of people who had marketplace coverage. You can only count what you actually paid out-of-pocket, not the gross premium amount. One last tip: if you're unsure about anything, getting official confirmation from the IRS (whether through their phone system, a professional, or services like the ones mentioned here) is always worth the time and effort. Better to be certain than to face penalties and interest later!

The discussion here is super helpful but there's one thing I haven't seen addressed: rental income. I have a similar situation (W2 plus consulting plus software sales), but I also own a couple rental properties. Does rental income qualify for QBI? Some accountants told me yes, others said no.

This is exactly the kind of complex QBI situation that trips up so many people! Diego, based on your income breakdown, you're definitely going to want to be strategic about this. Your W-2 income of $135k doesn't qualify for QBI at all - that's correct. For your self-employment income ($65k consulting + $70k software = $135k total), you're looking at potential QBI on that $135k, but with important caveats. The key issue is that your total income of $270k likely puts you above the phase-out thresholds ($170,050 single/$340,100 MFJ for 2023). This means your engineering consulting income will be significantly limited or eliminated from QBI since it's an SSTB. However, your software sales income might still qualify if it's truly product-based rather than service-based. The distinction others mentioned about custom vs. packaged software is crucial here. One strategy to consider: maximizing retirement contributions (SEP-IRA, Solo 401k) to potentially get your taxable income below the phase-out thresholds. Even a partial reduction could save you thousands. Also, make sure your CPA considers the W-2 wage limitation that applies at higher income levels - this could further complicate your QBI calculation even for the qualifying income streams. The tools others mentioned (taxr.ai, claimyr.com) seem worth exploring for the analysis, but definitely still work with your CPA for the final filing!