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I've used TurboTax Home & Business for the past 3 tax seasons with a similar mix of income sources. Honestly, it's pretty straightforward for your situation. The education expenses are simple to enter - it asks specific questions about your tuition and related expenses. For the self-employment portion, it breaks down common deductions by business type. Just make sure you've tracked your business expenses well throughout the year. The biggest hassle is entering all the individual expenses, but if you have good records it's not too bad. One tip: if you buy it through Amazon or Costco, you can often find it for $10-15 less than the list price!
Do you think TurboTax would catch something like the Qualified Business Income deduction? I've heard that's a big potential tax break for self-employed people, but I'm not sure if I qualify or how to calculate it.
TurboTax absolutely handles the Qualified Business Income deduction automatically. It determines your eligibility based on your business type and income level, then calculates the deduction without you needing to understand the complex rules. It also helps with things like the home office deduction (if applicable) and separates your self-employment tax calculations automatically. The software has gotten really good at guiding you through potential deductions with a simple interview process - it asks questions in plain English rather than tax jargon.
I was in this exact situation last year! I tried FreeTaxUSA instead of TurboTax and was really happy with it. It handled both my W-2 and self-employment income perfectly and cost WAY less than TurboTax. I think I paid about $15 for federal filing with self-employment, plus another $15 for state filing. The interface isn't quite as polished as TurboTax, but it asks all the same questions and covers education expenses, business mileage, and self-employment deductions thoroughly. Their support was also helpful when I had questions.
FreeTaxUSA is good but I found it doesn't give as much guidance for self-employment deductions. TurboTax specifically asks about industry-specific deductions you might miss otherwise. Worth the extra money in my experience since it saved me way more than the price difference.
Just to add some important info here: for legal settlements, it's crucial to understand that the tax treatment varies depending on what the settlement was compensating you for. According to IRS rules: 1. Compensation for physical injuries or physical sickness is NOT taxable 2. Emotional distress damages ARE taxable (unless they stem directly from physical injury) 3. Punitive damages ARE taxable 4. Lost wages/income ARE taxable OP, you mentioned this was a personal injury case with some emotional distress and punitive damages. You need to check your settlement documents to see if they specify how the money was allocated between these categories. Many settlement agreements don't break this down clearly, which is a major problem when it comes to taxes. If your settlement agreement doesn't specify the allocation, you should work with a tax professional to determine a reasonable allocation based on the facts of your case. This could significantly reduce your tax liability.
Thank you for breaking this down. My settlement documents aren't very clear about the allocation between physical injury, emotional distress, and punitive damages. I'm going to dig them up and review them again. Is there a specific section or wording I should look for that indicates how it's broken down?
Look for sections in your settlement agreement with headings like "allocation of settlement proceeds," "damages," or "consideration." Sometimes it's explicitly laid out, but often it's either vague or completely unaddressed. If there's no clear allocation, look for any language that describes the nature of your claim and what harms you suffered. Even terms like "physical injuries," "bodily harm," "emotional distress," or "punitive" can provide clues about what the settlement was intended to cover. If your documents really don't specify, don't panic. This is a common issue, and tax professionals who specialize in settlements can help establish a reasonable allocation based on the circumstances of your case. You'll want to gather any medical records, therapy bills, documentation of physical injuries, and information about lost wages to support your position on how the settlement should be allocated. Remember that the burden is technically on you to prove what portion was for physical injuries (and thus tax-free), so documentation is key. But don't assume the worst - many settlements are primarily for physical injuries and therefore largely non-taxable.
One thing nobody's mentioned yet - the timing of coming forward matters A LOT with the IRS. If you voluntarily file before they contact you, you're in a much better position than if they find you first. The Voluntary Disclosure Program can sometimes help reduce penalties. Also, since you mentioned having about $150k left, that might actually be enough to cover what you owe depending on how your settlement breaks down. Don't assume you'll owe taxes on the full amount. Lastly, don't panic about "the IRS hunting you down" - they're not the boogeyman. They deal with unfiled returns and late payments constantly. They have structured installment plans, and in some cases where people truly can't pay, they have programs like Currently Not Collectible status or Offer in Compromise to settle for less than you owe. It's a bureaucracy, and while they want their money, they have procedures for handling exactly your situation.
This is spot on. I worked for the IRS for 6 years, and I can tell you that most people's fear of the agency is way overblown. Agents are used to working with people who made mistakes. The worst thing you can do is hide - the best is to come forward voluntarily with a plan. I'd add one thing though: document EVERYTHING. Every call, every letter, every form you submit. Get names of agents you speak with. The IRS is a massive bureaucracy and things do get lost, so keeping your own detailed records is essential.
One important thing nobody mentioned is generation-skipping transfer tax considerations with trusts. If your parents are planning to leave assets to grandchildren or further generations, there's a separate GST tax that can apply at a flat 40% rate. Dynasty trusts can help with this by leveraging the GST exemption. My family used one to protect assets from estate taxes for multiple generations. We allocated our GST exemption to the trust when funded, and now those assets (which have grown significantly) can pass to grandkids and beyond without additional estate or GST tax.
That's really helpful, I hadn't even considered the generation-skipping aspect. My parents do have 3 grandchildren they'd like to provide for. How complicated was the setup process for your dynasty trust? And did you use an attorney with specific experience in this area?
The setup was definitely on the more complex end of the spectrum. We worked with an attorney who specializes in multi-generational wealth planning - not just any estate planning lawyer. The initial documentation was about 80 pages and took several meetings to finalize. I'd highly recommend finding someone with specific expertise in GST planning and dynasty trusts. These are specialized tools that general practitioners sometimes get wrong. In our case, we interviewed three different attorneys before choosing one. The right attorney will be able to balance tax advantages with practical family considerations like access to funds when needed.
Don't overlook the state estate tax angle. Federal exemptions are high, but states like Massachusetts, Oregon, and Minnesota have much lower exemptions (around $1-3 million). A properly structured trust can help with state estate taxes even if you're below the federal threshold.
This is so true. My parents got caught by this in Washington state. Their $3.5M estate was under the federal limit but still got hit with state estate tax. A credit shelter trust would have saved about $150k in state estate taxes when my dad passed.
When hiring a CPA on Upwork, look beyond just their credentials. I've had great and terrible experiences. One thing I recommend is giving them a "test question" about your specific tax situation before hiring them. See how they respond - do they give a detailed answer showing they understand the nuances? Do they ask clarifying questions? Or do they give vague, generic responses? Also, if you have international income or investments, make sure they have specific experience with FBAR filings and foreign income reporting. Those requirements can be super complicated and the penalties for mistakes are serious.
That's a great tip about the test question! What kinds of questions would you recommend asking to really test their knowledge? I do have some investment income but nothing international.
For investment income, ask them something specific about how different types of investments are taxed. For example: "I've been trading stocks regularly and also have some dividend income. Can you explain how these would be taxed differently and what forms I should expect?" A good CPA will explain the difference between short-term and long-term capital gains, ordinary vs qualified dividends, and mention forms like Schedule D and 1099-DIV. Another good test is asking about home office deductions if you work from home. The rules changed significantly after the Tax Cuts and Jobs Act, and a knowledgeable CPA should be able to explain the current rules and alternatives like the simplified deduction method.
Has anyone used a tax preparation service from Upwork that wasn't a CPA but still did a good job? I'm looking at some bookkeepers and tax preparers who seem to have good reviews but aren't certified CPAs.
I've used an Enrolled Agent (EA) for years and been very happy. EAs are federally licensed by the IRS specifically for tax preparation and representation. They often charge less than CPAs but are just as qualified for most personal tax situations. In fact, they sometimes have more specialized tax knowledge since CPAs also focus on accounting, auditing, etc.
Yara Assad
Another option to consider is using a low-interest credit card to pay the tax bill, especially if you can get a 0% intro APR card. I did this last year when I owed about $5k. Credit card processing fees were about 1.9% ($95), but then I had 18 months at 0% interest to pay it off. Worked out way cheaper than the IRS interest rate + penalties.
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Ingrid Larsson
ā¢Interesting idea! Do you know if there are specific credit cards that work better for this? I'd definitely consider this option if I could get approved for a decent limit.
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Yara Assad
ā¢Most major banks offer 0% intro APR cards if you have decent credit. Chase Freedom, Citi Simplicity, and Discover It all worked for me in the past. The key is making sure the 0% period is long enough for you to pay it off completely, and calculating whether the processing fee (usually 1.87-1.98% when paying taxes with credit card) is worth it compared to the IRS interest and penalties. For your $7,800 bill, you'd pay about $150 in processing fees, but then have no interest for 12-18 months depending on the card. Just be absolutely sure you can pay it off before the 0% period ends, because those interest rates will jump to 18-29% afterward.
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Olivia Clark
Don't forget about the IRS Fresh Start program! If you owe less than $50,000, you can get up to 72 months to pay. The interest still applies, but it's way better than collections. I set mine up online at irs.gov/payments and it was pretty simple.
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Javier Morales
ā¢Does anyone know if setting up a payment plan affects your credit score? I'm already dealing with some credit issues and don't want to make things worse.
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