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Marcus Marsh
Does anyone know if we can file normally (earlier than November) if we want to? My house was barely affected (just some minor leaking) and I'm actually expecting a pretty big refund this year. I'm in Santa Barbara County which is covered by the extension, but I'd rather get my refund sooner if possible.
Yes, you can absolutely file earlier! The November date is just the deadline - you can file anytime before then. If you're getting a refund, it definitely makes sense to file as soon as you're ready.
Cedric Chung
One important thing that hasn't been mentioned yet - if you make estimated tax payments, this extension also applies to those. So the Q1 and Q2 2025 estimated payments that would normally be due April 15 and June 15 are now also extended to November 16. This was a huge relief for me since my small business got hit hard by the flooding and cash flow has been a nightmare. Being able to delay those estimated payments while we rebuild is actually making a significant difference.
Talia Klein
ā¢Does anyone know if we'll get hit with an underpayment penalty if we don't make any estimated payments until November? Usually you're supposed to pay quarterly but this situation seems different.
Cedric Chung
ā¢Based on what I learned from the IRS when I called, you won't face underpayment penalties for delaying these specific estimated payments until November 16th. The disaster relief specifically waives penalties for these delayed payments. However, it's important to note that this only applies to the specific payment deadlines that fall within the relief period. Future estimated payments beyond this period would still follow the regular schedule and penalty rules.
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One thing nobody mentioned yet - make sure you're keeping good records of all your investment purchases and sales! The IRS requires you to track your "cost basis" (what you paid for the investment) to calculate your gains or losses accurately. Most brokerages now report this information to the IRS on Form 1099-B, but sometimes the information is incomplete or incorrect. I learned this the hard way when I couldn't prove my original purchase price for some stocks I'd held for years.
Do you have any tips for how to keep track of all this? I've been investing through multiple platforms (Robinhood, Vanguard, and a little crypto on Coinbase) and I'm worried about keeping everything straight for next year's taxes.
I recommend downloading annual tax documents from each platform and saving them in a dedicated tax folder on your computer. Name each file with the year and platform (like "2025_Robinhood_1099.pdf"). For crypto especially, consider using a dedicated tracking app that can integrate with multiple exchanges to create a comprehensive tax report. Some platforms like CoinTracker or Koinly can sync with Coinbase and other exchanges to track your cost basis automatically. The few minutes spent organizing throughout the year will save you hours of stress during tax season.
Justin Trejo
Quick tip: If you're married filing jointly, the capital loss deduction limit is still $3,000 total (not $3,000 per person). My spouse and I found this out when we tried to deduct $6,000 in losses and got our return rejected.
Alana Willis
ā¢Are you sure about that? My accountant let us deduct $3,000 each last year. Maybe the rules changed for the 2025 filing season?
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Omar Zaki
I'm a CPA who works with high-net-worth clients. One thing to consider that others haven't mentioned: you might actually need a team rather than just one person. In my practice, clients with your profile (real estate, trusts, private investments) typically work with: 1. A CPA for tax preparation and planning (quarterly, not just annually) 2. An estate attorney for trust structures and estate planning 3. A financial planner for investment strategy (even if you manage investments yourself) The key is finding a CPA who can quarterback this team and coordinate between specialists. Look for someone who specifically mentions "family office services" for clients who aren't quite wealthy enough for a dedicated family office but need comprehensive services. Also, consider whether you need someone registered as a fiduciary, which legally obligates them to act in your best interest. Not all financial advisors are fiduciaries.
This is a great point about needing a team. Do you recommend finding professionals who already work together or assembling my own team? I'm worried about coordination issues if everyone is working separately.
Omar Zaki
ā¢I strongly recommend finding professionals who already have established working relationships. Ask the CPA you're considering who they regularly collaborate with for estate planning and financial advice. Existing teams will have systems for sharing information efficiently and won't duplicate efforts. The worst scenario is having different advisors giving contradictory guidance. For example, I've seen situations where an investment advisor recommends selling assets that would trigger massive tax consequences the CPA would have advised against. When your team already works together, these issues get addressed before they become problems.
AstroAce
Has anyone used a CPA who specializes in real estate? I'm in a similar situation to the original poster but my biggest complexity is having properties in 3 different states. Tax filing has become a nightmare.
Chloe Martin
ā¢Check out the National Association of Real Estate Tax Professionals (NARETP). I found my CPA through them and it made a huge difference. Multi-state properties create special issues with depreciation tracking and state-specific rules that general CPAs often miss.
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Jamal Brown
Something nobody has mentioned yet - depending on your situation, you might want to consider recharacterizing your Roth IRA contribution to a Traditional IRA instead of just withdrawing the excess. Since you're filing jointly with your spouse, your combined income might allow you to deduct a Traditional IRA contribution, which could be beneficial. This way you don't lose the tax-advantaged space completely. Talk to your IRA provider about the "recharacterization" process. It's different from a withdrawal and has different tax implications. You'd still need to do this before the tax filing deadline (plus extensions).
That's an interesting option I hadn't considered. If I recharacterize to Traditional IRA, would I still need to worry about the earned income limit? And would I need to do anything special on my tax forms?
Jamal Brown
ā¢You still need earned income to contribute to a Traditional IRA, but the same limit applies - your contribution can't exceed your earned income for the year. So you'd still need to recharacterize the excess amount above your $4,200 income. For tax forms, you would report the recharacterization on your tax return using Form 8606 if any portion is non-deductible. Your IRA custodian will also send you a statement showing the recharacterized amount, which you should keep with your tax records. The good thing is recharacterization isn't a taxable event if done properly and before the deadline, so you avoid the penalties associated with excess contributions.
Just wanted to point out that if you already filed your 2023 taxes, you may need to file an amended return depending on how you handle the excess contribution. Some people just pay the 6% penalty and deal with it, but that's usually not the best approach since the penalty applies every year until you fix the issue.
Actually, if you withdraw the excess contribution plus earnings before you file your taxes (and before the due date), you don't need to file an amended return. You just report the earnings portion on your current year taxes. The IRA custodian will issue a 1099-R for the withdrawal.
Fiona Gallagher
About those 529 plans - while they don't give federal tax deductions, check if your state offers tax benefits! I live in NY and we get a state tax deduction up to $5K per year per beneficiary ($10K for married filing jointly). Made a huge difference on our state taxes.
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Thais Soares
ā¢This! I'm in Virginia and we get a $4,000 deduction per account on our state taxes. Definitely check your specific state rules - some states like Indiana even offer tax credits instead of deductions which are even better.
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Fiona Gallagher
ā¢Exactly right! State benefits vary hugely - Pennsylvania and Montana have unlimited deductions for contributions, while states like Colorado, New Mexico, and others offer deductions up to the annual gift tax exclusion amount. Some states require you to contribute to their specific 529 plan to get the benefit, while others (like Arizona and Kansas) give you the deduction regardless of which state's plan you use. I'd recommend calling your state tax department directly to confirm what's available. The tax savings might not be as big as federal deductions, but they definitely add up over time, especially if you're contributing for multiple children.
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Nalani Liu
For your property purchase idea, I did something similar buying a rental property. But don't just think about the mortgage interest deduction - consider the overall return. If you buy a $130k property with 20% down, your mortgage interest might only be $5-6k the first year, saving you maybe $1,300 in taxes if you're in the 22% bracket. But you could potentially also depreciate the property (except for the land portion), deduct property taxes, maintenance, insurance, etc. Plus hopefully the property appreciates in value and generates rental income. That's where the real benefit comes from. Don't buy property JUST for tax benefits - it needs to make sense as an overall investment.
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