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Yes, you can absolutely use TurboTax or TaxAct to file your 2020 and 2021 returns! I was in a similar situation last year with unfiled returns from 2019 and 2020. Here are the key things I learned: 1. You'll need to purchase the desktop software for each specific tax year - don't use the current year's software for prior years 2. Since you're owed federal refunds, there are no penalties from the IRS for filing late (they don't penalize you for being slow to collect money they owe you) 3. Your state penalties will vary, but most charge around 5% per month for failure to file plus interest The process is pretty straightforward once you get started. I'd recommend gathering all your documents first (W-2s, 1099s, receipts, etc.) for both years before you begin. You can file both years simultaneously - no need to wait for 2020 to process before submitting 2021. One tip: consider e-filing if the software allows it for those years, as it processes much faster than paper filing. Good luck getting this sorted out - it's not as overwhelming as it seems once you dive in!
Kai Santiago
β’This is really reassuring! I'm dealing with a similar mess - missed filing 2020 and 2021 due to some personal chaos, and like Juan, I'm pretty sure I'm owed federal refunds but will owe my state. Quick question: when you say "desktop software for each specific tax year," do you mean I need to buy TurboTax 2020 AND TurboTax 2021 separately? That seems expensive but if it gets this nightmare resolved, I'm willing to pay for it. Also, did you run into any issues with the IRS questioning why your returns were so late, or do they pretty much just process them without hassle once submitted?
Eve Freeman
β’Yes, you'll need to purchase separate software for each tax year - TurboTax 2020 and TurboTax 2021 as separate purchases. It does add up cost-wise, but it's necessary because each year's tax laws and forms are different. You can usually find older versions at a discount compared to the current year. As for the IRS questioning late filings - they really don't care as long as you don't owe them money. When you're getting a refund, they process it just like any other return. No interrogation, no special paperwork explaining why it's late. The only time they get pushy is when you owe them money and haven't paid. Your state is a different story though - they'll definitely charge penalties and interest since you owe them, but again, no questioning about why it's late. They're just happy to finally get their money plus the extra fees!
Just wanted to share my experience as someone who went through this exact situation! I had unfiled returns for 2019, 2020, and 2021 due to a combination of job loss and family health issues. Here's what worked for me: 1. **TaxAct was cheaper than TurboTax** for multiple prior years - saved me about $60 total compared to TurboTax's pricing for older versions. 2. **Gather everything first** - I spent a weekend collecting all my tax documents before starting anything. Having everything organized made the process so much smoother. 3. **State amnesty programs are real** - My state (Michigan) had a voluntary disclosure program that cut my penalties in half. Definitely worth checking if your state offers something similar. 4. **E-file worked for both 2020 and 2021** - Got my federal refunds in about 3 weeks each, which was way faster than I expected for late returns. The whole thing took me about 2 weeks from start to finish, and honestly, the anticipation and dread was worse than actually doing it. You've got this! The software walks you through everything step by step, and since you're getting federal refunds, the IRS will be happy to send you your money once you file. One last tip: If you have any self-employment income or complicated deductions, consider getting a tax pro to review everything before you submit. Sometimes the extra cost is worth the peace of mind.
Chloe Taylor
β’Thank you for sharing such detailed info! I'm curious about the state amnesty programs - how did you find out about Michigan's voluntary disclosure program? Did you have to search their tax department website specifically, or is there a general resource that lists which states offer these programs? I'm in Texas and wondering if they have something similar that could help reduce my penalties.
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TommyKapitz
Anyone know if this also applies to the additional Medicare tax? I'm above the threshold for that too and wondering if that gets handled the same way when switching employers.
The Additional Medicare Tax is handled differently! Unlike regular Social Security tax, there's no refund mechanism if multiple employers cause you to overpay the Additional Medicare Tax. Each employer is required to withhold the 0.9% Additional Medicare Tax on wages they pay you over $200,000, regardless of your filing status or wages from other employers. If your total income doesn't actually exceed the threshold for your filing status, you'll get any overpayment back when you file your tax return. But if your total income does exceed the threshold, you might actually owe more, not less.
Emma Wilson
This is exactly what happened to me two years ago when I switched from a startup to a big tech company mid-year. The frustrating part is watching your new colleagues celebrate their "SS tax holiday" while you're still getting hit with the full deduction! One thing I learned the hard way - make sure you keep detailed records of your pay stubs from both employers throughout the year. When tax season came around, I had to dig through months of pay stubs to calculate the exact overpayment amount. Having everything organized made the refund process much smoother. Also, if you're using tax software, most of the major ones (TurboTax, H&R Block, etc.) will automatically calculate your excess Social Security tax refund when you enter your W-2 information. They'll flag it and walk you through claiming it on Schedule 3. Just double-check their math - I caught a small error one year that would have cost me about $200. The silver lining is that you essentially get an interest-free loan to the government that you'll get back at tax time. Not ideal, but at least it's not lost money!
Ally Tailer
β’Great advice about keeping detailed records! I'm actually going through this exact situation right now and wish I had seen this earlier. Quick question - when you mention that tax software will automatically calculate the excess, does it handle situations where you have bonuses that pushed you over the cap at different times? My compensation is pretty bonus-heavy and I'm worried the timing might complicate things. Also, has anyone dealt with this when one of the employers was a contractor situation (1099) versus W-2? I did some freelance work early in the year before my full-time job and I'm not sure if that affects the Social Security tax calculations.
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Sole proprietorship is the simplest business structure but just remember you'll need to pay self-employment tax (about 15.3%) on your photography income. Even if it's under $1k, you still need to report it.
Owen Jenkins
β’Wait, self-employment tax is 15.3%?? That seems super high. Is that on top of regular income tax? I thought since I made less than $1,350 I might not even need to report it.
Yes, self-employment tax is 15.3% which covers Social Security and Medicare taxes. When you work for an employer, they pay half of this and you pay half, but as a self-employed person, you cover the entire amount. This is in addition to your regular income tax. However, there's good news - you only have to file and pay self-employment tax if your net earnings are $400 or more. So if your photography income after expenses is less than $400, you wouldn't owe self-employment tax. But you should still report the income on your tax return regardless of the amount. Those equipment deductions might actually bring your net profit below the $400 threshold, which would save you from owing the self-employment tax.
Don't forget you can also write off other stuff besides just equipment! I do wedding photography and deduct my website costs, part of my cell phone bill, mileage to/from shoots, lightroom subscription, business cards, etc.
Isaac Wright
β’Can you write off education costs too? I took some online photography courses to improve my skills.
Diego Chavez
β’Yes, you can absolutely deduct education costs! Online photography courses, workshops, tutorials, and even books related to photography are all legitimate business education expenses. Just keep your receipts and make sure the education is directly related to your photography business. I deducted a $300 lighting workshop last year and it passed my audit without any issues.
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Lily Young
Remember that gambling income is taxable even if you didn't get a W2G form. The IRS requires you to report ALL gambling winnings, even small amounts. Player cards at casinos can also track your activity.
Ana ErdoΔan
β’what about online gambling?
Lily Young
β’Online casinos still report to IRS if you win over $1,200 in one go. They have your SSN when you signed up.
Nia Wilson
The IRS gets copies of all W-2G forms that casinos issue for winnings over $1,200 (slots/bingo) or $5,000 (poker tournaments). Your transcript will definitely show these reported amounts even before you file your return. If you had $50k in wins, that's likely already in their system. Best to get your transcript now and see exactly what they have on file - you can request it free directly from IRS.gov. Don't risk penalties by underreporting what they already know about.
This is super helpful info! I'm new here but dealing with a similar situation. Quick question - when you say "get your transcript now", how long does it usually take to receive it? And is there a difference between what shows up on the online transcript vs the mailed version? Want to make sure I'm seeing everything before I file.
Yara Campbell
Your situation is actually quite common and you're being smart to think about this proactively. The fact that you specifically purchased a larger home to accommodate the Airbnb business is a strong indicator of profit motive that would help in any IRS review. A few thoughts on strengthening your position: 1. **Documentation is key** - Keep detailed records of time spent on the business (guest communication, cleaning, maintenance, marketing). This shows it's not a hobby. 2. **Your 40% allocation seems reasonable** if it's based on actual square footage used exclusively for the rental. Just make sure you have a simple floor plan or measurement documentation to support this. 3. **Consider showing some profit in 2025** - Even a small profit would help reset the "hobby loss" clock. Maybe slightly reduce some discretionary expenses or be more aggressive with pricing. 4. **Track improvement efforts** - Document any changes you make to increase profitability (pricing adjustments, marketing spend, property improvements). This shows business intent. The IRS knows rental properties can have legitimate losses, especially in the early years or during market downturns. Your repeated efforts and the fact that this isn't enjoyable work for you both support treating this as a business. Just keep good records and consider making 2025 a profitable year if possible.
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GalacticGuru
β’This is excellent advice! I'm curious about the "reset the hobby loss clock" concept you mentioned. If I show a profit in 2025, does that actually reset the 3-out-of-5-years safe harbor rule, or would the IRS still look at my overall pattern of losses from 2020-2024? Also, regarding the documentation of time spent - do you recommend tracking this in any particular format? I've been pretty informal about recording my hosting activities, but it sounds like I should be more systematic about it going forward.
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GalacticGuru
β’Great question! The 3-out-of-5-years test uses a rolling 5-year window, so a profit in 2025 would help but wouldn't completely erase your loss pattern. The IRS would look at 2021-2025, where you'd have 2 profitable years out of 5 (2019 falls outside the window). While this still doesn't meet the safe harbor, it significantly strengthens your position. For time tracking, I'd recommend a simple spreadsheet or app like Toggl. Track categories like: guest communication (check-ins, questions, reviews), cleaning/maintenance, marketing/pricing research, and administrative tasks (bookkeeping, supply ordering). Even 15-30 minutes here and there adds up and shows serious business effort. The key is consistency - start tracking now and continue forward. If questioned, being able to show "I spend 8-12 hours per month actively managing this business" is much more compelling than "I do a lot of work but don't track it." Some hosts I know discovered they were spending way more time than they realized, which really helped support their business classification.
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QuantumQuest
Your situation definitely warrants careful attention, but you have several strong factors working in your favor. The intentional purchase of a larger home specifically for Airbnb use is excellent evidence of profit motive - this isn't someone who accidentally started renting out a spare room. A few additional strategies to consider: **Strengthen your business records:** - Create a simple business plan outlining your strategy for profitability - Document market research showing how you set rates and respond to competition - Keep receipts and photos of property improvements that enhance rental appeal **Consider operational changes:** - Analyze if you can optimize your pricing strategy (dynamic pricing tools, seasonal adjustments) - Track your occupancy rates and guest satisfaction scores as business metrics - Document any efforts to reduce operating costs while maintaining quality **Regarding your 40% allocation** - this is reasonable if based on actual exclusive-use space. Just ensure you can support it with measurements or floor plans. The reality is that many legitimate rental businesses show losses in early years, especially when factoring in depreciation. Your profits in 2018-2019 show this wasn't set up as a tax shelter, and the recent losses coincide with broader market challenges many hosts are facing. Consider making small adjustments to show even a modest profit in 2025 if possible - sometimes reducing discretionary expenses or being more aggressive with rates can make the difference between a small loss and small profit, which significantly strengthens your position.
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Kennedy Morrison
β’This is really comprehensive advice! I'm particularly interested in the dynamic pricing tools you mentioned. Are there specific platforms you'd recommend for Airbnb hosts? I've been manually adjusting my rates based on what I see other properties charging, but having a more systematic approach would definitely help demonstrate business-like operations to the IRS. Also, when you mention documenting market research, would screenshots of competitor listings and pricing be sufficient evidence, or should I be keeping more formal records? I want to make sure I'm building the right kind of documentation trail in case I ever need to defend my business classification.
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Logan Chiang
β’For dynamic pricing, I'd recommend looking into tools like PriceLabs or Beyond Pricing - they automatically adjust your rates based on local market conditions, events, and demand patterns. The key benefit for IRS purposes is that these platforms generate reports showing your pricing strategy over time, which is excellent documentation of business-like operations. For market research documentation, screenshots are actually perfect! Create a monthly folder with competitor pricing screenshots, noting the dates and your reasoning for any rate adjustments. Even a simple spreadsheet tracking "Date | My Rate | Competitor A Rate | Competitor B Rate | Reason for Change" shows systematic business decision-making. Also consider documenting seasonal patterns, local events that affect demand, and guest feedback that influences your pricing or property improvements. The IRS loves to see evidence that you're actively managing the business to increase profitability rather than just passively collecting rental income. One tip: if you use dynamic pricing tools, keep the reports they generate. They often show data on market penetration, rate optimization suggestions you followed, and revenue performance compared to similar properties - all great evidence of profit-seeking behavior.
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