I've used Column Tax for exactly 3 tax seasons, including this one. They had precisely 2 major system updates this year which I believe caused the issues we're seeing. I tracked 17 different deductions for my small business, and 4 of them disappeared in the final return. Their customer service took exactly 8 business days to respond, but they did eventually fix everything. I'd recommend everyone double-check their returns against what was actually submitted to the IRS.

I'm dealing with the exact same issue! Filed through Column Tax via MoneyLion in February and my Schedule C business deductions are completely missing from the final return. What's really frustrating is that I can see all my entered deductions in their interface, but when I downloaded the actual PDF that was submitted to the IRS, half of them aren't there. I've been trying to reach their support for over two weeks with zero response. Has anyone successfully gotten Column to resubmit a corrected return, or do we all need to file amendments at this point? This is exactly why I'm hesitant to use these integrated fintech tax services - when something goes wrong, you're stuck in limbo between two companies pointing fingers at each other.

Dealt with this exact issue for my 2020 filing. I found a middle ground by asking my CPA to just charge me their hourly rate instead of per transaction. Ended up paying around $400 total for a return with 300+ trades since I had everything organized from my brokers already. Maybe ask your preparer if they'd consider an hourly rate alternative? If they refuse, that's a red flag that they're just trying to milk you for cash.

As someone who's been through this exact nightmare, I can confirm you're absolutely being taken for a ride. $10 per transaction is highway robbery, especially when modern tax software can import and process hundreds of trades in minutes. I had a similar situation with 2019 taxes (also filed late) where I had over 400 options trades across multiple platforms. My first preparer quoted me $3,500 using the same per-transaction scam. I walked away and found a CPA who charged me a flat $250 fee for all investment reporting because I came prepared with organized statements. Here's what I learned: Most brokerages provide exportable transaction files that can be directly imported into tax software. The "manual entry" excuse is outdated - preparers who claim they need to enter each trade individually are either using stone-age software or trying to inflate their fees. For your 2020 return specifically, don't let the late filing pressure you into accepting ridiculous fees. You have options: - Shop around for preparers who charge flat fees for investment reporting - Use tax software like TurboTax or FreeTaxUSA that handle bulk imports - Ask your current preparer for an hourly rate instead Those 2020 COVID credits are worth pursuing, but not at a $2000+ markup for basic data entry work.

The LLC structure won't help you bypass the passive activity loss limitations since the IRS focuses on the substance of the activity, not the entity form. However, there are a few other strategies worth exploring for your situation. Since you're already maximizing depreciation on the rental portion and plan to pass the property to your kids, consider whether the current tax benefits outweigh the depreciation recapture you'd face if you ever sold. The stepped-up basis strategy you mentioned is solid for estate planning. One often overlooked opportunity is ensuring you're capturing all allowable expenses for the rental portion - home office deductions if you use part of your space for rental management, travel expenses to purchase supplies, etc. Also, make sure you're properly allocating utilities, maintenance, and insurance between personal and rental use. Given your income level, you might also want to explore whether either you or your spouse could qualify as a real estate professional by documenting time spent on rental activities. Even if it's just property management, maintenance coordination, and tenant screening, those hours can add up. The 750-hour threshold is more achievable than many people think when you properly track all real estate-related activities.

I've been following this thread with great interest as I'm in a very similar situation - primary residence with rental income that exceeds the passive loss limitations. One strategy that hasn't been mentioned yet is potentially converting your current setup into a legitimate boarding house or bed & breakfast operation. If you can document that you're providing substantial services to your tenants (daily cleaning, meals, utilities management, etc.), the rental income might be reclassified as active business income rather than passive rental income. This would allow you to deduct losses against your other income regardless of the $150k threshold. The key is that you need to provide services that go beyond what a typical landlord provides. Things like furnished rooms with daily housekeeping, shared common areas you actively maintain, or meal preparation can help establish this as an active business rather than passive rental activity. Obviously this changes the nature of your living arrangement significantly, and you'd need to check local zoning laws and HOA restrictions. But for the right situation, it could be a way to legitimately convert passive losses into active business deductions while keeping the property in your name for the eventual stepped-up basis benefit you're planning for your children.

I understand you're in a tough spot, but I'd really encourage you to step back and consider if this is the right move. Even though your employer doesn't require documentation, the IRS still has the final say on what qualifies as a hardship withdrawal, and car loan payments typically don't make the cut unless you're facing imminent repossession that would prevent you from working. Here's what I'd suggest before touching your 401k: Contact your car lender immediately to discuss options - many will work with you on payment deferrals, loan modifications, or extended payment plans, especially if you explain your situation. Also look into refinancing with a credit union, which often offers better rates and terms than traditional lenders. If you absolutely must access retirement funds, consider if your plan allows 401k loans instead (I know you mentioned you're maxed out, but sometimes there are different loan categories). The interest you pay goes back to your own account, and there's no penalty or tax consequences if you repay on time. The math is sobering - that $14,500 withdrawal will cost you roughly $16,000-18,000 after taxes and penalties, plus you lose decades of compound growth. That same amount could be worth $80,000+ by retirement age. If you do move forward despite these risks, document everything showing this withdrawal addresses an immediate and heavy financial need, not just convenience. Keep records of any repossession threats, proof you need the car for work, and evidence you explored all other options first.

I've been following this thread and wanted to add some perspective from someone who works in retirement plan administration. The key issue everyone's touching on is that the IRS has a two-part test for hardship withdrawals: 1) immediate and heavy financial need, and 2) the withdrawal amount doesn't exceed what's necessary to meet that need. While paying off a car loan generally doesn't qualify, there are situations where it might - specifically if you're facing imminent repossession and can demonstrate that losing the vehicle would create severe hardship (like being unable to work, get medical care, etc.). The documentation would need to show the immediate threat and why alternative solutions aren't viable. That said, I'd strongly echo the advice about exploring refinancing first. Many lenders will work with borrowers facing hardship - payment deferrals, term extensions, or even principal reductions in some cases. Credit unions are especially good at this. The long-term cost of the 401k withdrawal (taxes, penalties, plus lost growth) will likely far exceed any savings from paying off the loan early. If you do proceed, keep meticulous records showing: the immediate financial crisis, why the car is essential, what alternatives you explored, and any repossession threats. Even though your employer doesn't require documentation, the IRS might during an audit, and you want to be prepared to justify this as a legitimate hardship rather than just debt consolidation.

This is such a common frustration! I went through the exact same thing with my year-end bonus last month. The key thing to remember is that the high withholding you're seeing (that 40%) is just your employer being overly cautious - it's not the actual tax rate you'll pay on the bonus. Most employers use the "aggregate method" which treats your bonus like it's your regular weekly/monthly pay. So if you got a $10,000 bonus, they withhold as if you make that much every pay period all year long, which temporarily bumps you into a much higher tax bracket for withholding purposes. When you file your taxes, that bonus just gets added to your regular income and taxed at your normal marginal rates. So if you're truly in the 24% bracket, that's what you'll actually pay on the bonus income. The extra withholding becomes a nice refund! I know it stings to see so much taken out upfront, but think of it as forced savings that you'll get back with interest (well, without interest, but you get the idea). At least you won't owe anything come April!

I had the exact same shock when I got my bonus last year! Seeing nearly 40% disappear was heart-breaking, especially after working so hard to earn it. What helped me understand this better was learning that there are actually two different withholding methods employers can use for bonuses. The flat 22% rate you found in your research is one option, but most employers use the "aggregate method" instead. This method combines your bonus with your regular paycheck and calculates withholding as if that combined amount was your normal pay every period. So if you normally make $5,000 per month and get a $10,000 bonus, the payroll system calculates taxes as if you make $15,000 every month ($180,000 annually). That temporarily pushes you into higher withholding brackets, which is why you're seeing that 40% rate. The good news is that when you file your taxes, your bonus gets taxed exactly the same as your regular income - no special "bonus tax rate." It all goes into the same bucket and gets taxed according to your actual tax brackets. So you'll likely get a nice refund of that over-withholding! I know it doesn't make the initial sting any less painful, but at least you know you're not actually losing that money permanently.