As someone new to this community, I've been following this discussion closely since I'm in a similar situation with my own 1098-T. What really strikes me is how unanimous everyone has been about not misrepresenting the scholarship information - and for good reason based on all the experiences shared here. The automated matching systems that several people mentioned are honestly quite sobering. It sounds like the IRS has made it nearly impossible to slip anything past them when it comes to education credits, especially with how schools report directly to them. What I found most valuable was learning about all the legitimate expenses beyond tuition that can qualify for credits. I had completely overlooked things like required software, lab equipment, and mandatory fees that aren't always captured on the 1098-T. After reading through these responses, I'm going to go back through my own expenses to see what I might have missed rather than even considering misrepresenting anything. The peace of mind of filing correctly definitely seems worth more than any short-term financial gain, especially when you factor in the potential penalties, interest, and stress of dealing with an audit down the road. Thanks to everyone who shared their experiences and expertise - it's really helped clarify the smart approach here!

As a newcomer to this community, I want to thank everyone for sharing such detailed and honest experiences about 1098-T issues. Reading through all these responses has been incredibly educational and frankly, quite sobering about how risky it would be to misrepresent scholarship information. What really stood out to me was learning about the automated matching systems between what schools report and what taxpayers claim. I had no idea the IRS had such sophisticated detection capabilities for education credits specifically. The insight from @Zara Rashid about universities actually getting contacted when there are discrepancies really drives home how interconnected these systems are. I'm particularly grateful for all the practical advice about legitimate expenses that often get overlooked - required software, lab equipment, mandatory fees not captured on the 1098-T, and course materials. It's clear that many students (myself included) probably miss out on credits they're actually entitled to because we don't realize what qualifies beyond just tuition. The personal stories about audit experiences and penalties really emphasize that any short-term financial gain isn't worth the long-term stress and costs. I'll definitely be taking the conservative approach and carefully reviewing what legitimate expenses I can claim rather than considering any questionable reporting. This community seems incredibly knowledgeable and supportive - looking forward to learning more from everyone's expertise!

Has anyone had success asking their mortgage company to pay the property taxes in the correct tax year? I'm in a similar situation where my county always sends bills late (usually December) but my mortgage company sometimes waits until January to pay them, which messes up my tax deductions.

I'm dealing with almost the exact same situation! My county sent out 2023 property tax bills in February 2024, and my mortgage company just paid them last month. Really frustrating to potentially lose out on deductions because of government delays. One thing I'm wondering - has anyone looked into whether there's any recourse against the county for the late billing? It seems like their delay is what's causing all these tax complications for homeowners. I know it won't help with this year's taxes, but maybe there's a way to push for more timely billing in the future. Also, for those mentioning the SALT cap issues - I'm curious if anyone has calculated whether it's actually worth switching from escrow to paying property taxes directly to have more control over timing. The mortgage company discount on my rate is pretty small, so it might be worth the flexibility.

Can you reach out to any other family members who might be able to help as a go-between? Sometimes having a neutral third party can help in these situations. Otherwise Form 4852 is exactly what it's designed for - situations where you can't get a W-2 but need to file your taxes.

I'm dealing with a similar family business situation right now, so I really feel for you. One thing that might help is checking if your family's business uses any payroll service like ADP, Paychex, or QuickBooks Payroll. Sometimes you can get your W-2 directly from the payroll company's website even if you can't contact your employer directly. Also, if you have any old login credentials for a payroll portal or employee self-service site, those might still work. I was able to download my W-2 from our family business's ADP portal even after leaving because they never deactivated my account. If those options don't work, Form 4852 really is your best bet. The IRS designed it specifically for situations like yours where getting the W-2 isn't realistic. Just be as accurate as possible with your estimates and keep any documentation you have (paystubs, bank deposits, etc.) in case they ask questions later.

Thanks for all the helpful responses everyone! Just wanted to give a quick update - I went ahead and used my husband's SSN (primary taxpayer) in Direct Pay and the payment went through smoothly. Got a confirmation number and everything. I really appreciate everyone clarifying that even though I'm the one earning the freelance income, the IRS system only recognizes the primary taxpayer's info for joint filers. That makes total sense now that I understand how their computer systems work. I'm definitely going to look into some of the tools mentioned here (like taxr.ai) to help me calculate the right amounts for future quarters. I've been kind of winging it with estimated payments and want to make sure I'm not underpaying and getting hit with penalties. One last question - should I be making these payments every quarter even if my freelance income varies a lot month to month? Sometimes I have big projects and sometimes barely anything. Is it better to estimate conservatively and potentially overpay, or try to match the actual income more precisely each quarter?

One thing I'd add to the safe harbor discussion - you can also use the "annualized income installment method" if your freelance income is really sporadic throughout the year. This lets you calculate each quarterly payment based on your actual income for that specific period, rather than spreading an annual estimate evenly across four quarters. It's more paperwork (you'll need to file Form 2210 with your return), but it can save you money if most of your income comes in just one or two quarters. For example, if you have a huge project in Q3 but barely any income in Q1 and Q2, you could make smaller payments early in the year and a larger payment in Q3 when you actually earned the money. The downside is it's more complex to calculate and track. For most people with moderately variable income, the safe harbor approach that Mateo mentioned is much simpler and still protects you from penalties. But if your income swings are really dramatic (like making 80% of your annual freelance income in one quarter), the annualized method might be worth looking into.

This has been such an incredibly thorough and educational discussion! As someone who's been dealing with NOL carryforwards from a business that didn't work out as planned, I really appreciate how comprehensively everyone has covered the NOL and capital gains intersection. The key takeaways I'm getting are: 1) Yes, NOLs can offset capital gains including from real estate sales, 2) There's an 80% limitation for post-2020 NOLs, 3) State tax rules may differ significantly from federal rules, and 4) The optimization requires looking at multiple years, not just the current tax year. What really strikes me is how this discussion evolved from a basic question about NOL rules into a masterclass on integrated tax planning. The interactions with NIIT, depreciation recapture, suspended passive losses, Roth conversions, and even broader investment strategy considerations show just how interconnected tax planning really is. I'm definitely going to follow the advice about getting comprehensive multi-year tax projections rather than just a consultation. Given all the variables discussed here, it's clear that optimizing NOL usage properly requires professional modeling that accounts for federal taxes, state taxes, timing strategies, and your broader financial goals simultaneously. Thanks to everyone who shared such detailed expertise - this is exactly the kind of collaborative knowledge-sharing that makes complex tax decisions much more manageable!

This has been an absolutely phenomenal discussion that's covered virtually every angle of NOL and capital gains planning! As someone who works in tax preparation during the busy season, I wanted to add a few practical insights that might help others in similar situations. One thing that hasn't been fully emphasized is the importance of timing your NOL usage with your overall income pattern. If you expect to be in a higher tax bracket in future years (due to business recovery, spouse returning to work, etc.), it might make sense to preserve some NOLs for those higher-income years, even with the 80% limitation. Also, for those dealing with multiple types of carryforwards (NOLs, capital loss carryforwards, charitable contribution carryforwards), the order of application matters and can affect your optimization strategy. NOLs are generally applied after most other deductions, which can create some interesting planning opportunities. Finally, I'd strongly recommend documenting your NOL planning decisions and rationale. The IRS has been increasing scrutiny of NOL claims in recent years, especially for taxpayers with significant carryforward amounts. Having clear documentation of your planning process and professional advice can be invaluable if questions arise later. The collaborative expertise shared in this thread has created an incredibly valuable resource for anyone dealing with NOL complexities. This is exactly why professional communities like this are so important for navigating our ever-changing tax landscape!