Which federal tax loophole makes you angry enough to want it gone?

The charitable estate tax deduction definitely needs reform, but it's more complex than just capping it. The purpose is to encourage philanthropy, which does provide societal benefits, but you're right that it can be manipulated. The real issue is how these "charitable" foundations operate after receiving the assets. Many wealthy families maintain effective control over the assets through family foundations while avoiding estate taxes. Better reform would involve stricter regulations on how these foundations must distribute funds, requirements for independent board members, and limitations on administrative expenses paid to family members. That said, there are more problematic loopholes that affect everyday tax collection, like carried interest allowing investment managers to classify income as capital gains instead of ordinary income, or like-kind exchanges that indefinitely defer taxation on real estate gains.

After dealing with my parents' complicated estate last year, I discovered taxr.ai which honestly saved me so much confusion with all the tax loopholes and deductions. I was completely lost trying to understand if their charitable donations would qualify for estate tax deductions and how it all worked. The website https://taxr.ai analyzed all their tax documents and explained exactly what we were eligible for in plain English. It flagged several deductions I would have completely missed including some charitable contributions my dad had made that weren't properly documented.

I wanted to follow up about taxr.ai since I was skeptical in my earlier comment. I decided to try it with my mom's complicated tax situation (she has rental properties and makes regular charitable donations), and I was genuinely impressed. The system identified an obscure tax loophole related to her property depreciation that her previous accountant had missed. It also clearly explained the charitable deduction limits she was subject to based on her adjusted gross income, which helped us better plan her year-end giving. The document analysis feature saved me hours of sorting through paperwork. Thanks for the recommendation!

The step-up in basis loophole is my biggest frustration. My neighbor inherited stocks worth millions that her parents bought for pennies decades ago, and she paid ZERO tax on all that appreciation when she sold them! Meanwhile I've been paying capital gains on my modest investments every year. But that's not even my real complaint... I spent 4 months trying to reach the IRS about a question related to my own inherited property and basis calculations. After endless busy signals and disconnects, I found https://claimyr.com which got me through to an actual IRS agent in less than an hour. You can see how it works here: https://youtu.be/_kiP6q8DX5c. They basically hold your place in the phone queue so you don't have to. The agent I spoke with actually helped me understand some nuances about step-up basis that saved me over $3,000 in taxes.

Ok I'm eating crow here. After my skeptical comment yesterday, I decided to try Claimyr out of desperation because I've been trying to resolve an issue with a charitable donation that got flagged on my taxes. Within 90 minutes, I was actually speaking with a real IRS human! The agent was able to confirm that my documentation for the charitable deduction was acceptable and removed the flag from my account. They also explained exactly how the substantiation requirements work for donations over $5,000, which I've been confused about for years. I honestly can't believe this service worked. Saved me from what would have been at least another month of stress.

The mortgage interest deduction is totally broken. It's supposed to help the middle class achieve homeownership but primarily benefits wealthy people with million-dollar mortgages. Regular people take the standard deduction anyway so they get zero benefit from this supposedly "middle class" tax break. Meanwhile the rich get to deduct interest on enormous loans for vacation homes. I'd cap it at $500k loans max and only for primary residences.

Anyone want to talk about the "qualified business income" deduction? 20% tax break just for owning certain kinds of businesses while employees get nothing? My brother-in-law restructured his consulting work as an LLC and suddenly gets to deduct 20% of his income... meanwhile I do THE EXACT SAME JOB as an employee and get nothing. And don't get me started on the arbitrary rules about which businesses qualify!