The IRS has definitely made progress, but you're right that it still feels clunky compared to modern websites. One thing that helped me navigate their site better was using the search function instead of trying to follow their menu structure - it actually works pretty well now. For what it's worth, the IRS did invest heavily in modernizing their systems over the past few years, but they're dealing with decades of legacy infrastructure. The Direct File program Sofia mentioned is actually a sign they're moving in the right direction - it has a much more intuitive interface than the main IRS site. If you do end up needing to use their tools, I'd recommend bookmarking the specific pages you need (like Where's My Refund) rather than trying to navigate there from the homepage each time. It's not perfect, but it's definitely better than the old site that looked like it was built with HTML tables!

I completely understand your frustration! I was in the exact same boat until this year. The good news is that 2025 has actually brought some major improvements to electronic filing options that weren't available before. First, definitely check out the IRS Direct File program that others mentioned - it's genuinely free and covers way more situations than the old Free File options. I was skeptical at first, but it handled my return (including some investment income) without any issues or hidden fees. For the signature issue specifically - most e-filed returns now use electronic PINs instead of physical signatures. You create a secure PIN during the filing process that serves as your legal signature. The only time you really need a wet signature anymore is for certain amended returns or very specific forms. If you do have forms that absolutely must be mailed, here's a pro tip: send them certified mail with return receipt requested. It costs a few extra dollars but you'll have proof they received it and won't be left wondering if your return got lost in the mail. The IRS processes certified mail faster too since it goes to a different queue. The whole system is definitely still more complicated than it should be, but we're finally moving away from the paper-heavy process. Don't give up on electronic options - they really have improved dramatically in just the past year!

What happens if both people try to claim the mortgage interest? My gf and I split the mortgage payments (she's on the loan, I'm not), and her 1098 obviously shows the full interest amount. If I try to claim my portion as an "equitable owner" and she claims her portion, will that trigger problems?

I've been following this thread closely since I'm in a very similar situation. One thing I want to add that hasn't been mentioned much is the importance of timing when creating your written agreement. While you don't need to backdate anything, I'd strongly recommend creating that ownership agreement ASAP before you file your taxes. The IRS looks favorably on contemporaneous documentation - meaning paperwork that exists at the time the situation is happening, not created after the fact when you're trying to justify a tax position. Also, make sure your agreement is specific about percentages. Don't just say "in exchange for mortgage payments, I have an ownership interest." Be clear: "In exchange for paying 100% of the mortgage payments, I am entitled to X% ownership interest in the property's equity." This specificity will help a lot if you ever get questioned. One last tip - consider having your girlfriend explicitly state on her tax return that she's NOT claiming the mortgage interest deduction because someone else (you) is claiming it as an equitable owner. This coordination between your returns shows the IRS you're not trying to hide anything.

Have you tried logging into your H&R Block online account? Sometimes you can see the disbursement details there. Or maybe check your email for a receipt from when you filed? I need to figure this out too for next year. Did you specifically request the refund to be transferred to your bank after it hits the Emerald Card?

I had this exact same confusion with H&R Block two years ago! Here's what actually happens: when you pay that $42 refund transfer fee, your refund will definitely go to the Emerald Card first - that's how their system works. The IRS sends your refund to H&R Block's temporary account, they deduct their fees, then put the remainder on your Emerald Card. From there, if you set up a transfer to your bank account during filing, it should automatically move to your bank within 1-3 business days. But if you didn't specifically request that transfer, the money will just stay on the Emerald Card. Check your filing paperwork or log into your H&R Block account online to see what transfer option you selected. The automated system is telling you the truth - it goes to the card first, then potentially to your bank depending on your choices.

The key thing to remember is that your 1099-NEC filing obligation is completely separate from whatever Venmo does or doesn't report. As a business owner, you're required to issue 1099-NECs to any non-employee service provider you paid $600 or more during the tax year - period. The payment method is irrelevant. Whether you paid via personal Venmo, business Venmo, check, cash, or carrier pigeon, your reporting requirement stays the same. Venmo's 1099-K reporting (which only applies to business accounts anyway) is about THEIR obligation to report payment processing volume, not about YOUR obligation to report business expenses. So for your makeup artist ($7,800) and assistant ($5,200), you definitely need to issue 1099-NECs. Get their W-9 forms ASAP and file the 1099s by January 31st. Don't overthink the Venmo aspect - just focus on the basic rule: $600+ to a service provider = 1099-NEC required.

Just to add some practical tips for collecting those W-9s: I've found it helpful to explain to contractors WHY you need the form rather than just demanding it. Most freelancers understand it's for tax compliance, but newer ones sometimes get worried you're "reporting them to the IRS" when really you're just following standard business practices. I usually send an email saying something like "Hi [Name], I need to collect W-9 forms from all service providers who received over $600 from my business this year for tax reporting purposes. This is a standard IRS requirement for businesses. Could you please fill out the attached form and return it by [date]?" Also, keep digital copies of all W-9s in a secure folder - you'll need the information for years to come, and contractors sometimes change their contact info or business structure. Having everything organized makes tax season much smoother. One last thing: if any of your contractors are LLCs or corporations, you may not need to issue 1099-NECs depending on their entity type. The W-9 will show their tax classification and help you determine the requirement.

The debate about flat taxes is fascinating, but I think we need to consider what "fairness" actually means in taxation. From my perspective as someone who's worked in both high and low-paying jobs, the current progressive system recognizes that $1,000 means very different things to someone making $30,000 versus someone making $300,000. A true flat tax with zero exemptions would essentially be a regressive system in practice. When you're spending 80% of your income on basic necessities like rent, food, and healthcare, taxing that remaining 20% at the same rate as someone who spends maybe 30% on necessities feels fundamentally unfair. I keep thinking about this: if we eliminated the mortgage interest deduction, charitable deduction, and other complex provisions that mainly benefit higher earners, but kept basic protections like the standard deduction and earned income credit, wouldn't that achieve most of the simplification benefits without hurting working families? Sometimes I wonder if the "flat tax" conversation is really about simplification or if it's actually about shifting the tax burden downward.

As someone who's been following tax policy discussions for years, I think this conversation really highlights why nuanced policy analysis matters more than catchy slogans like "flat tax simplicity." The reality is that our current system, while complex, has evolved to address real-world inequities. When people say the bottom 50% only contribute 3% of revenue, they're missing the point - that's actually evidence the system is working as intended to protect those with the least ability to pay. I've noticed that most serious flat tax proposals end up including some form of exemption or "prebate" system precisely because pure flat taxation would be devastating to working families. At that point, you're not really implementing a flat tax anymore - you're just redesigning the progressive system with fewer brackets. What strikes me about this thread is how valuable it's been to see people actually run their numbers rather than just debating in the abstract. Whether through AI tools, IRS consultations, or international comparisons, the concrete examples show that tax policy isn't just about simplicity - it's about balancing revenue needs with economic fairness and social outcomes. Maybe instead of pursuing a flat tax, we should focus on targeted simplification: eliminate complex deductions that primarily benefit high earners while preserving the credits and exemptions that help working families. That seems like a more practical path to both simplicity and fairness.