What would you change about the tax code? Asking for some creative ideas for simplification!

What about student loan interest deduction? That phase-out seems really low to me and it's above-the-line which is different from other deductions. Would your standardized phase-outs apply there too? Also what income definition would you use – AGI, MAGI, or something new?

Great question about student loan interest. Yes, I'd include that in the standardized phase-outs. The current threshold is ridiculously low considering today's education costs and salary levels. It phases out so quickly that many graduates lose it right when they start making decent money. I'd use a modified AGI but with fewer adjustments than the current system. Something closer to total income minus only the most essential adjustments. The problem with having multiple definitions (AGI, MAGI, etc.) is that each tax benefit uses a slightly different calculation, which is exactly the complexity we need to eliminate.

How exactly does it work? Do you just upload your tax documents and it tells you things you might have missed? I'm self-employed with rental properties and feel like I'm always missing deductions.

Sounds too good to be true honestly. Can it really find things that professional tax software misses? What makes it better than TurboTax or whatever?

It works by analyzing your tax documents and identifying optimization opportunities based on your specific situation. You upload your relevant tax documents, and it scans them for potential deductions, credits, and strategies you might have missed. It's especially helpful for complex situations like yours with self-employment and rental properties. What makes it different from regular tax software is that it doesn't just process what you input – it actively looks for optimization opportunities based on your documents and suggests strategies you might not know about. Unlike TurboTax which basically just fills out forms based on what you tell it, this actually reviews your documents to find things you didn't know to look for.

Wait what? How does this actually get you through to the IRS faster? Isn't the whole problem that their phone lines are completely jammed?

Sounds scammy. The IRS phone system is the same for everyone. How could a third party possibly get you through faster? And why would anyone pay for that?

It uses technology to navigate the IRS phone system and waits on hold for you. When it reaches a live person, it calls you and connects you directly to that IRS agent. So instead of you personally waiting on hold for hours, their system does it for you. The IRS phone system is jammed, but the service basically automates the process of calling repeatedly, navigating the menus, and waiting on hold so you don't have to tie up your phone and waste your day. It's not skipping the line - it's just handling the frustrating waiting process for you.

The married filing separately thing is interesting! I've rarely seen cases where it's beneficial. But what about separated couples who aren't legally divorced yet? Would you have some exception for them?

Good point about separated couples! I'd create a simple "legally separated" status that would essentially treat them as single filers. The current system with MFS is just too punitive with all its limitations and phase-outs. The problem is that MFS was designed to prevent gaming the system, but it's become so restrictive that it actually creates unfair outcomes for people in difficult situations, like those separating or dealing with a spouse who won't cooperate on taxes. A better-designed single status for separated individuals would be much more straightforward.

Average cost basis would be amazing! Also why are crypto transactions so complicated tax-wise? I bought and sold some Bitcoin last year and the tax calculations were insane. Each transaction created a taxable event and I had hundreds.