That would have been a good option, but it's too late now - I already sold the property about 6 months ago. I was just hoping there might be a way to avoid getting stuck with a big tax bill since I was basically just following my mom's instructions and didn't keep any of the profits.

That's unfortunate timing. For future reference (or for anyone else reading this thread), always consult with a tax professional BEFORE making property transfers between family members. These transactions are complex and can have significant tax consequences. Since the sale has already happened, your best option now is probably to gather all documentation showing that you were acting on your mother's behalf. While this doesn't eliminate your tax liability, good documentation might help if there's ever an audit. Make sure you have the quitclaim deed, documentation of the original basis (purchase price plus improvements), the sales contract, and proof that you transferred the proceeds to your mother and other family members.

The step transaction doctrine actually might work against OP in this case. The IRS could view the series of transactions (mother gifts to OP, OP sells and distributes money) as an attempt to avoid proper tax treatment. Since the legal ownership was transferred to OP before the sale, OP is technically the seller for tax purposes. The subsequent distribution of funds is considered separate. This arrangement actually creates more tax complications than if the mother had sold it directly and then gifted portions of the proceeds. What might help OP's case is documenting that they were acting under a power of attorney or as a fiduciary for their mother, but that would need to have been established properly before these transactions occurred.

This is really helpful, thank you! Do you think it's better to amend the returns to married filing jointly or just remove the excess contributions? We've been filing separately because my spouse has an income-based student loan repayment plan, so filing jointly would increase those payments. But maybe the Roth IRA penalties would be worse?

Whether to amend to MFJ or remove excess contributions depends on your complete financial picture. You need to calculate both scenarios to see which costs less overall. For the student loan consideration, calculate how much the income-based payments would increase if filing jointly versus the cost of Roth IRA penalties (6% per year on excess contributions) plus any potential tax benefits lost by filing separately. Sometimes it's cheaper to pay higher student loan payments for a year than pay IRS penalties and miss out on tax credits only available to joint filers. This is definitely a situation where running the numbers both ways is essential before deciding.

Yes, I got hit with this exact situation last year. The IRS sent me a CP2000 notice about unreported income, and during that review, they flagged my Roth contributions while I was MFS with income over $10k. Ended up with penalties for 3 years of contributions plus interest. It was a mess to clean up, so I recommend being proactive before they find it.

Thanks for breaking it down like that! So would real estate commissions count as selling costs? And do I need specific documentation for all this or can I just put the numbers in when I file?

Yes, real estate commissions definitely count as selling costs! They're usually one of the biggest deductions from your sale proceeds. Other selling costs that reduce your amount realized include legal fees, transfer taxes, and any seller-paid closing costs. Documentation is important. You should keep your closing statements from both the purchase and sale (HUD-1 forms or Closing Disclosures), plus receipts for any improvements you made to the property. You don't submit these with your tax return, but you'll need them if you're ever audited. When you file, you'll report this on Schedule D and possibly Form 8949, depending on your situation.

You'll report it on Schedule D (Capital Gains and Losses) and possibly Form 8949 (Sales and Other Dispositions of Capital Assets) depending on your situation. Most tax software will guide you through this when you indicate you sold land or real estate. The important thing is to have your purchase information (date, cost, closing costs) and your sale information (date, proceeds, selling expenses) ready.

10 Is there any way to reduce the tax hit? I'm thinking about surrendering a policy but worried about having to pay a lot in taxes. Can I roll it over into something else tax-free?

22 Yes, you have a couple options to potentially reduce or defer the tax impact. If your policy qualifies, you could do what's called a 1035 exchange into an annuity or another life insurance policy. This allows you to transfer the cash value without triggering immediate taxation. Another option is to see if your policy allows for partial surrenders over multiple tax years instead of taking all the money at once. This can spread the tax liability across different years and potentially keep you in a lower tax bracket. Just be aware that each partial surrender can affect your overall basis calculation in complex ways.

9 Unfortunately, surrender fees typically aren't tax deductible. They're just considered a reduction in your proceeds. So if your surrender value is $5,000 but you only get $4,400 after surrender charges, you'll only pay taxes on the gain based on the $4,400 you actually receive (minus your basis).

Is this really legit though? Don't you have to run actual payroll with proper tax withholdings at the time you take the money? I've been stressing about making sure everything is by-the-book with my new S-Corp.

This is absolutely legitimate as long as you properly document and account for everything. When you run payroll, you'll calculate the full gross salary amount, withhold all required taxes, and then reduce the net check by the amount you already advanced yourself. For example, if your reasonable salary is $5,000 monthly and you already took $3,000 as an advance, when you run payroll, you'll still calculate taxes on the full $5,000, but the net check would only be around $2,000 (minus the taxes on the full amount). This ensures all proper employment taxes are paid on your full reasonable compensation. Just make sure your payroll system can handle this "adjustment" or "reimbursement" properly.

Agreed! I did something similar my first year and my accountant just had me document everything carefully. The important thing is the year-end picture looks right. S-Corps get in trouble when they take massive distributions and tiny salaries over the course of entire years, not when they make minor timing errors while learning the ropes.