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Be careful with tax relief companies! My cousin paid $5,000 to one of those places you see advertised on TV, and they basically just filled out forms he could have done himself. They promised to get his $40k tax debt down to $5k but in the end, they just got him on a payment plan. The IRS actually has taxpayer advocates that can help you for FREE. Call 877-777-4778 and they can assist with navigating your options. Saved me a ton of money when I was in a similar situation last year.
Do you need to qualify for the Taxpayer Advocate Service? I thought they only help in hardship situations or when you've been trying to resolve an issue for a long time without success.
You're right that the Taxpayer Advocate Service typically helps with hardship situations or cases where you've made multiple attempts to resolve an issue with the IRS without success. They prioritize cases where people are facing immediate negative financial impact, like the threat of losing housing or transportation. In most tax debt situations, especially ones with liens or levies threatened, you'll likely qualify for their help. But even if you don't qualify for their full service, they can still point you toward the right resources. They're one of the few truly free options available, and they work for the taxpayer, not the collection division of the IRS.
Has anybody tried DIY tax resolution? I'm considering just calling the IRS myself and trying to negotiate my tax debt down. I owe about $18,000 and don't have much income right now.
I did this successfully last year. Called the IRS (took forever to get through) and set up a payment plan for $22,000. First, I requested Currently Not Collectible status which they granted for 6 months when my income was really low. Then I set up a $250/month payment plan after I got a new job. They were actually reasonable to work with once I finally reached someone.
I tried the DIY approach and messed it up badly. Filed the wrong form for an OIC and got rejected, which reset my collection timeline. I think it depends on how complicated your situation is and how comfortable you are with tax forms.
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Ethan Wilson
Don't forget about state taxes too! Everyone's talking about federal returns but you probably need to file state returns for those years as well. Each state has different thresholds for who needs to file.
Diego Rojas
ā¢Ugh you're right, I totally wasn't even thinking about state taxes. Do I need to file state returns for every state I lived in during that time? I moved twice in the last few years.
Ethan Wilson
ā¢Yes, you'll need to file in each state where you lived and earned income. If you moved mid-year, you might need to file part-year resident returns in both states for that year. Most states follow similar rules to federal for filing thresholds, but some have much lower income requirements. You'll want to file the state returns for the same years as your federal returns. Many states have their own tax forgiveness or amnesty programs that might help reduce any penalties if you owed taxes. Some states also had their own stimulus programs during COVID that you might have missed.
NeonNova
FYI - definitely get your Pell Grant info in order. If you used the money for anything besides tuition, fees, books, and required supplies, you might owe taxes on that portion. Like if you used some for rent or food.
Yuki Tanaka
ā¢How would the IRS even know what you used the Pell Grant money for? I just got a lump sum deposited to my account every semester.
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Ana Rusula
10 I was in almost the exact same situation a few years ago! Based on my experience, here's what you should consider: With a duplex split 50/50, you'll likely do better with the standard deduction for your personal half unless you have significant other itemizable expenses (like major medical expenses or large charitable donations). The rental side is reported separately on Schedule E where you can deduct expenses regardless of whether you take standard or itemized deduction. Don't forget about depreciation on the rental portion! That's a big deduction many new landlords miss. And definitely take advantage of your Montana residency - that's a smart military tax move.
Ana Rusula
ā¢1 Thanks for the advice! I didn't even think about depreciation. Is that something I calculate myself or do I need an accountant? And are there any military-specific deductions I should know about with this setup?
Ana Rusula
ā¢10 Depreciation is actually pretty straightforward for residential rental property. The IRS lets you depreciate the building portion (not the land) over 27.5 years. You'll need to determine what portion of your purchase price was for the building vs. land - your property tax assessment often breaks this down, or you can use a reasonable estimate like 80% building/20% land in most areas. As for military-specific deductions, you can deduct unreimbursed moving expenses (still available for military even though civilians lost this deduction), and you may be able to exclude combat pay if applicable. If you paid state taxes in non-resident states where you were temporarily stationed, you might get credits for those in certain situations. I'd recommend talking to a military-experienced tax professional your first year with this setup.
Ana Rusula
22 Has anyone here used any particular tax software that handles the military + rental property situation well? I've used TurboTax in the past but it seems confused when I try to enter my duplex info and military status.
Ana Rusula
ā¢24 I've tried several and had the best luck with FreeTaxUSA. It handles the Schedule E for rentals really well and asks all the right questions about military service. Plus it's way cheaper than TurboTax especially if you have rental income - TurboTax forces you into their premium version for that.
Ana Rusula
ā¢22 Thanks! I'll give FreeTaxUSA a try. TurboTax was charging me nearly $200 for the premium version plus state filing, which seems excessive considering we get free filing options through Military OneSource.
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Olivia Kay
Another option to consider: If you're using accounting software like QuickBooks, you can actually record this properly there first and it'll flow correctly to your tax forms. Here's how: 1. Record the purchase of the new laptop at full price ($1,450) 2. Record the trade-in as a "sale" of the old asset for $325 3. Make sure your old laptop has the correct remaining book value in your system The software will handle the calculations and depreciation correctly. This is what I do for all my business equipment, and it makes tax time so much easier.
Does this work the same way if I use FreshBooks instead of QuickBooks? I find the asset tracking in FreshBooks a bit confusing for trade-ins.
Olivia Kay
ā¢FreshBooks handles fixed assets a bit differently than QuickBooks. In FreshBooks, you'll need to create a new expense for the full amount of the new laptop, then create a "credit" entry for the trade-in value. It's not as automated for calculating the remaining book value, so you'll need to know the remaining undepreciated value of your old laptop. If you're using FreshBooks, I'd recommend creating a simple spreadsheet on the side to track your fixed assets, their original purchase prices, accumulated depreciation, and current book values. This makes it much easier at tax time and ensures you're reporting everything correctly when you have trade-ins or sales of business equipment.
Jibriel Kohn
Just to add a real-world example - I just went through this with my 2023 taxes. I traded in my old business MacBook ($2,100 original cost, depreciated to about $840 book value) for a new one that cost $2,300. Got $750 trade-in. The IRS considers this a "like-kind exchange" of business property. I deducted the full $2,300 for the new laptop, and had to recognize a small gain since my trade-in value ($750) was more than my remaining book value ($840). My accountant said as long as you have good records showing the original cost, depreciation taken, and the trade-in value, you're fine. The only tricky part is if you used the old laptop partially for personal use - then you have to allocate.
Thanks for the example! Did you handle this with regular depreciation or did you use Section 179 to expense the whole thing in the first year? Also, did you have to fill out any special forms for the "like-kind exchange" part?
Jamal Harris
Another option that nobody's mentioned is that you can create an online account on the IRS website and access your tax records that way. Go to IRS.gov and look for "View Your Account." You'll need to create an ID.me account or login.gov account if you don't already have one. The verification process is kind of a pain (you need to upload ID and do a video selfie), but once you're in, you can see your tax records for multiple years. That's how I get mine without dealing with TurboTax's fees.
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Mei Chen
ā¢The ID.me verification is actually why I couldn't get my transcript online! They couldn't verify my phone for some reason and I got stuck in this endless loop. Has anyone found a workaround for the ID.me verification issues?
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Jamal Harris
ā¢The ID.me system can definitely be frustrating. If you're having trouble with the automated verification, try their "video chat verification" option. It lets you speak with a human representative who can manually verify your identity. It takes longer (sometimes there's a waiting room), but it usually works when the automated system fails. Another option is to use the login.gov pathway instead of ID.me if it gives you that choice. Some people have better luck with one system versus the other.
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Liam Sullivan
Am I the only one who thinks it's ridiculous that we have to jump through all these hoops just to get copies of OUR OWN tax returns??? The tax prep companies charge us to prepare the returns, then charge again to access them later, and the IRS makes it incredibly difficult to get copies directly from them. The whole system seems designed to be as frustrating as possible!
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Amara Okafor
ā¢It's not just you! The tax system in the US is deliberately complicated because tax prep companies lobby to keep it that way. Many other countries have simple tax filing systems where the government pre-fills your forms and you just verify them. But companies like H&R Block and TurboTax literally spend millions lobbying to prevent simplification because it would hurt their business model.
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Liam Sullivan
ā¢I had no idea about the lobbying thing, but it makes total sense. I lived in Sweden for a few years and filing taxes there took like 5 minutes - they sent me a pre-filled form and I just confirmed it was correct by text message. Coming back to the US tax system was a huge shock. I'm definitely going to be more careful about saving copies of everything from now on. Lesson learned the hard way!
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