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3 Worth mentioning - if you had a lot of medical expenses this year but they don't quite push you over the standard deduction threshold, consider "bunching" your deductions. This means trying to concentrate deductible expenses in a single tax year. For example, if you know you'll have medical procedures early next year, see if you can prepay them in December of this year. Same with charitable donations - make next year's donations in December of this year. That way, you might have enough to itemize one year, and then take the standard deduction the next year.
18 Question about bunching - does this actually save money in the long run? Or does it just shift when you get the deduction?
3 Bunching can definitely save money in the long run! Let me explain with an example. Say you have $10,000 in medical expenses each year for two years, and the standard deduction is $12,900. If you take those expenses in separate years, you'd take the standard deduction both years ($12,900 Ć 2 = $25,800 total deductions). But if you could bunch $20,000 of expenses into one year, you'd itemize that year ($20,000) and take the standard deduction ($12,900) the next year, for a total of $32,900 in deductions across two years. That's an extra $7,100 in deductions!
7 Have you looked into an HSA (Health Savings Account)? It won't help with expenses you've already paid, but for future medical costs, it's WAY better than itemizing deductions. Contributions are pre-tax, grow tax-free, and withdrawals for medical expenses are tax-free too. Triple tax advantage!
1 I've been considering an HSA but I'm not sure if I qualify. Don't you need a high-deductible health plan for that? I have insurance through my employer but not sure what type of plan it counts as.
I'm using Credit Karma Tax (now called Cash App Taxes) this year. Completely free for federal AND state returns, which is what initially drew me to it. Been using it for 3 years and it handles my moderately complex situation well (W-2 income, some stock sales, mortgage interest, etc). The interface is clean and they don't try to upsell you since it's completely free. Only downside is they don't support some more complex situations like multi-state filing or foreign income. But for most people, it's a great option that costs literally nothing.
Does Cash App Taxes handle self-employment income well? I have a small side business and have been using TurboTax Self-Employed, but it's so expensive.
Yes, Cash App Taxes handles self-employment income quite well for straightforward situations. It has all the Schedule C forms and walks you through business deductions, home office calculations, and quarterly estimated payments. Where it might fall short is if you have very complex business situations like inventory management, multiple businesses, or specialized industry deductions. For a side gig bringing in $4k like the original poster mentioned, it would be perfectly fine. I have a photography side business that makes about $12k annually and it works great for me.
Am I the only one still using a local CPA? I tried software for years but kept missing deductions. Started using a local accountant 3 years ago and she finds way more savings than I ever did on my own. I pay $350 for my return which includes a rental property and some self-employment income, but she saves me at least $1500 in taxes compared to when I did it myself. Plus when I got a letter from the IRS questioning something on my 2021 return, she handled everything for no additional fee. The peace of mind alone is worth it to me.
Do you think a CPA is worth it for simpler returns? I just have a W-2 job and a mortgage, no complicated stuff.
I used a CPA last year and she missed a huge education credit I was eligible for. When I pointed it out she acted like I was being difficult. Going back to doing it myself this year.
5 Don't forget that this all assumes you're itemizing deductions rather than taking the standard deduction! With the standard deduction at $13,850 for single filers and $27,700 for married filing jointly in 2023, many people don't benefit from itemizing anymore unless they have very high mortgage interest, state taxes, or charitable contributions. Make sure your total itemized deductions (including this margin interest) exceed your standard deduction amount, otherwise all this calculation work won't actually save you anything on your taxes.
11 Great point! I actually messed this up last year. Spent hours tracking investment interest and other itemized deductions only to have my tax software automatically take the standard deduction because it was higher. Felt like such a waste of time.
5 Excellent reminder! To add a bit more detail - even if you can't benefit from the deduction this year because you're taking the standard deduction, you should still complete Form 4952 to establish your carryforward amount for future years when you might itemize. Also worth noting that if you're in a high-tax state like California, New York, or New Jersey, you're more likely to benefit from itemizing since state and local tax payments (though capped at $10,000) plus your margin interest might push you over the standard deduction threshold.
15 Something important that hasn't been mentioned yet - make sure you're not running afoul of the "investment purpose" requirement. The IRS requires that margin loans be used specifically for investment purposes to be deductible. If you're using margin for personal expenses (like buying a car or paying for a vacation), that portion of the interest isn't deductible as investment interest. I learned this the hard way after an audit where I had to prove my margin loans were used to purchase securities.
2 Is there a specific way to document this? My brokerage account is kind of a mess with deposits, withdrawals, and margin usage all mixed together throughout the year.
One thing to consider is getting your returns prepared professionally before submitting them. I did my back taxes myself using TurboTax and missed several deductions I could have claimed. A friend had H&R Block do his unfiled returns and they found nearly $4,000 in deductions he missed because he didn't know what to look for. If money is tight, look into the Volunteer Income Tax Assistance (VITA) program or the Tax Counseling for the Elderly (TCE) program which offer free tax preparation for qualifying taxpayers.
Do these free tax prep services handle back taxes from previous years? I thought they only did current year returns during tax season.
You're right that many VITA and TCE sites focus primarily on current year returns during the regular tax season. However, some locations do offer assistance with prior year returns, though this varies by site. You'd need to call specific locations to ask about their services for back tax returns. If free services aren't available for prior years in your area, consider a low-cost tax professional instead of the major chains - often local enrolled agents or CPAs will handle back taxes for much less than the big tax preparation companies, especially for straightforward returns.
Has anyone actually received one of those scary "Intent to Levy" notices after not filing? I'm in a similar boat (3 years unfiled) and just got one of these notices that's freaking me out. Says they can seize property, bank accounts, etc!!!
I got one of those last year. It's scary but doesn't mean they're immediately coming for your stuff. You usually have 30 days to respond, and if you call them and show you're trying to fix the situation by filing and setting up payments, they'll often put a hold on collection activities.
Anastasia Fedorov
I've actually tried both plus H&R Block and TaxAct over the years. For simple returns, my ranking would be: 1. FreeTaxUSA - best value, good interface, all forms included 2. TaxAct - decent middle ground 3. H&R Block - okay but getting expensive 4. TurboTax - most expensive, aggressive upselling FreeTaxUSA isn't as pretty but functionally works great. The only advantage TurboTax has is importing investment forms can be easier if you have lots of them. For basic W-2 income, some interest or dividends, and standard deductions, FreeTaxUSA is honestly better because it's straightforward without constant attempts to upgrade you.
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StarStrider
ā¢What about audit protection? TurboTax always scares me into buying their audit defense. Does FreeTaxUSA offer something similar or is it not really necessary?
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Anastasia Fedorov
ā¢FreeTaxUSA does offer audit assistance (they call it "Deluxe") for around $7-8 which is MUCH cheaper than TurboTax's audit defense. It provides priority support and help with audit-related questions if you get audited. Honestly though, for simple returns, your audit risk is extremely low. The IRS mostly targets unusual deductions, self-employment with weird numbers, or very high income returns. If you're just filing W-2 income and standard deductions, the audit risk is tiny. I personally don't buy audit protection anymore for basic returns, but the FreeTaxUSA version is cheap enough if it gives you peace of mind.
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Sean Doyle
I used FreeTaxUSA last year after 4 years of TurboTax and it was fine for my situation (W-2, mortgage interest, student loan interest, some stocks). The ONLY thing I missed from TurboTax was the automatic import of W-2 information - with FreeTaxUSA I had to manually enter everything. But that took like an extra 10 minutes total and saved me $70+ so definitely worth it. Also, FreeTaxUSA doesn't try to hide fees until the end like TurboTax always did to me. They're upfront about state filing costs from the beginning. Customer service was surprisingly good too when I had a question about reporting some crypto.
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Zara Rashid
ā¢Did you notice any difference in refund amount between what you got with TurboTax vs FreetaxUSA? I always worry cheaper software might miss deductions or something.
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