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Just FYI - I paid a large tax bill last year (around $97k) and the IRS Direct Pay system worked perfectly, but my bank flagged it as suspicious and froze my account for 48 hours! Make sure to call your bank BEFORE making the payment to let them know a large transaction is coming. Would have saved me a massive headache.
That's a really good point I hadn't considered. My bank has done that before with much smaller purchases that were "out of pattern" for me. Did you have to provide any specific info to your bank when you called them?
I just had to tell them the approximate amount, the date I planned to make the transaction, and that it would be going to the US Treasury. They made a note on my account and the payment went through without any issues after that. Some banks might want more details like the exact routing number for the Treasury, but mine didn't need that. Just make sure to call at least 24 hours before you plan to make the payment so they have time to note your account properly.
Has anyone tried paying with a credit card for the points/rewards? With a $150k bill, those rewards could be substantial, right? I know there's a processing fee but might be worth it?
Bad idea. The processing fees for tax payments by credit card are around 2% - that's $3,000 on a $150k payment! Even the best reward cards only give 1-1.5% back, so you'd actually LOSE money. Plus many credit cards won't even have a limit high enough for that payment.
Also keep in mind that the IRS limits you to 2 credit card payments per tax period, and some processors have maximum amounts they'll process. You'd probably have to split it up and pay multiple fees. Definitely not worth it.
I worked at a bank that got acquired (not First Republic but similar situation) and had some stock in my Roth IRA too. One thing nobody's mentioned - can you roll over your Roth IRA to another provider and possibly get some better investment options to help rebuild what you lost? I moved mine to Fidelity and their advisors helped me rebalance with some funds that have performed pretty well since then. Won't fix the tax situation but might help recover some value over time.
That's actually a really helpful suggestion! I hadn't thought about switching providers, but it makes sense to look for better investment options. Did you have any fees when you moved your Roth IRA to Fidelity? And how long did the whole process take?
No fees to transfer the Roth IRA to Fidelity - most major brokerages don't charge for incoming transfers. The whole process took about 2 weeks from starting the paperwork to having everything settled in the new account. Fidelity handled most of the transfer work once I filled out their forms. The good part was getting access to their research tools and fund options. I met with one of their advisors (free consultation) who suggested a portfolio mix based on my retirement timeline that's been working well.
Don't forget that while you can't deduct the ROTH IRA losses, you still have all the contributions you've made available to withdraw at any time without taxes or penalties. That's one of the biggest advantages of a Roth vs traditional IRA. If you really need access to some funds, you can withdraw your contributions (but not earnings) without any tax consequences. Just make sure to check exactly how much you've contributed over the years so you don't accidentally withdraw any earnings.
This is a really important point! I had a similar situation happen and it's easy to focus on the loss and forget that the money you put in is still accessible if needed.
One thing to keep in mind - make sure you're getting the W-9 forms from the ACTUAL property owner, not just the management company. I made this mistake with my pop-up shop and issued 1099s to the wrong entity. Had to amend everything and it was a huge headache. Also, some malls are owned by REITs (Real Estate Investment Trusts) which have different tax reporting requirements. Definitely worth asking specifically about this when you collect their info.
Thanks for bringing this up - good point! How do I verify I'm getting the W-9 from the actual property owner? The lease agreement I sign is always with the mall management company.
The lease agreement can be tricky because sometimes the management company is authorized to sign on behalf of the property owner. You should specifically ask "Who is the legal owner of this property that will be reporting the rental income for tax purposes?" That question usually clarifies things. The W-9 itself will also tell you - look at the name and tax ID. If it's a different entity than what's on your lease, ask for clarification. Sometimes the management company will provide a letter explaining the relationship between the entities if they're affiliated.
Has anyone dealt with situations where different mall locations are owned by the same parent company? I'm wondering if I add up all the rental payments to different locations owned by the same company when determining if I've hit the $600 threshold?
Yes, you would aggregate payments to the same legal entity. So if Mall A and Mall B are both owned by XYZ Properties Inc., you'd add up all payments to XYZ when determining if you've exceeded $600. That's why getting those W-9s is so important - to identify when different locations have the same ultimate payee.
That makes sense, thanks for the clarification! Guess I need to start tracking these payments by parent company instead of just by location.
Something else to consider - was your hubby required to file last year? If his income was below the filing threshold, he might not have actually been required to file at all. For 2023, a single person under 65 didn't need to file if income was under $13,850. Different thresholds apply based on filing status (married, head of household, etc).
This is super important! My brother thought he was in trouble for not filing but it turned out his income was below the threshold so he wasn't even required to. Saved him tons of stress!
When you file the late return, make sure you write the tax year (2023) clearly on the top of the form! The IRS processes millions of returns and you want to make sure they apply it to the correct tax year. Also, if he does owe money and can't pay it all at once, you can request an installment agreement by filing Form 9465 with the late return. This lets you make monthly payments instead of paying the full amount immediately. Don't wait any longer to file though - the longer you wait, the more complicated it gets!
Lauren Johnson
Has anyone actually calculated how much tax you end up owing on forgiven debt? Like for $10,000 in forgiven debt, what would the actual tax bill be? I'm in a similar situation but with about $7,000 in forgiven medical debt.
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Jade Santiago
ā¢It depends on your tax bracket. The forgiven debt gets added to your other income for the year. So if you're in the 22% federal tax bracket, you'd pay about $2,200 on $10,000 of forgiven debt (plus any state taxes). But definitely check if you qualify for insolvency first!
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Caleb Stone
IMPORTANT: Keep in mind the 1099-C should be issued for the year the debt was actually cancelled, not when they decided to send you the form. I had a creditor send me a 1099-C for debt they forgave two years earlier, and it caused all kinds of problems. If the forgiveness happened in a previous tax year, you might need to file an amended return for that year instead of including it on this year's taxes.
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Daniel Price
ā¢This happened to me too! The credit card company sent me a 1099-C in 2023 for debt they actually cancelled in 2022. I had to file an amended return and it was such a hassle. Check the "Date of Identifiable Event" box on your 1099-C form - that's the date that matters for tax purposes, not when they sent the form.
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KhalilStar
ā¢Thanks for pointing this out! I just double-checked my 1099-C and the date listed is from this year, so I think I'm okay. But good to know for everyone else that the date on the form matters!
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