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One strategy that worked well for my electrical contracting business was setting up a Cash Balance Plan in addition to our 401(k). Last year I was able to contribute over $150,000 pre-tax between the two plans. It's especially effective when you're in those higher tax brackets. Also, make sure your brother-in-law is tracking meals properly. Construction businesses can often deduct 100% of certain meals (not the standard 50%) when they're for jobsite employees. My CPA caught this and it saved us about $7k last year.
That's really interesting about the Cash Balance Plan - I've never heard of that before. Is there a specific income threshold where it makes sense to set one up? And is it something that can be established quickly before year-end?
Cash Balance Plans generally make the most sense when your income is consistently over $300,000, though the benefits increase substantially at higher income levels. They're especially valuable for business owners in their 40s or 50s who need to catch up on retirement savings. Setting one up requires some lead time - typically 2-3 months for the plan design and legal documentation. While it's getting tight for this tax year, it's still possible if he acts immediately. The contribution deadline would be the business tax filing deadline (including extensions), but the plan must be established before year-end to count for this tax year.
Cedric Chung
Something nobody has mentioned yet - if your brother-in-law does a lot of government/public works contracts, he might qualify for certain credits or deductions related to those projects. My construction company primarily does municipal work and we qualify for several incentives including some energy-efficiency credits when we incorporate certain materials or methods. Also, has he considered restructuring some of his personal expenses? For example, if he frequently entertains clients at his home, a portion of his housing costs might be deductible. Or if family members legitimately work in the business, spreading income among family can reduce the overall tax burden.
Talia Klein
ā¢The home deduction suggestion seems risky. I tried that a few years ago and got audited. The IRS is super picky about what qualifies as a legitimate home office deduction.
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Zoe Gonzalez
3 I had this exact situation last year. The key is understanding that Vanguard (and most brokerages) don't track which part of your Roth IRA is contributions vs. earnings - they just report the total distribution with code J. For TurboTax specifically, when it asks for the distribution type, you want option 3 (return of contributions). Make sure you also have good records of your total Roth contributions over the years to prove that your withdrawal didn't exceed your contribution basis if you ever get audited!
Zoe Gonzalez
ā¢12 Do you know if I need to file any additional forms besides just entering this in TurboTax? I'm worried about doing it wrong and getting a surprise tax bill or audit.
Zoe Gonzalez
ā¢3 You don't typically need to file any additional forms if you're using software like TurboTax - it will generate all required forms when you complete the interview questions correctly. The key form is Form 8606 Part III, which TurboTax will create once you indicate it's a return of Roth contributions. Just make sure you keep good records of your total Roth contributions over time. I recommend creating a simple spreadsheet tracking all your contributions by year, so if you're ever audited, you can prove that your withdrawal didn't exceed your total contribution basis.
Zoe Gonzalez
9 One thing nobody mentioned yet - check if Box 2a (Taxable amount) on your 1099-R shows $0. If it does, that's good! Vanguard is telling the IRS they believe this is a non-taxable distribution. If it shows another amount, you'll need to be more careful in how you report it.
Zoe Gonzalez
ā¢14 Good point. Mine shows $0 in Box 2a but has the distribution code J which seemed contradictory to me. That's why I got confused.
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Chloe Wilson
Check if your employer is withholding state taxes too! I had a similar issue last year where they weren't taking out federal OR state taxes. Fixed the federal part but completely forgot about state and got hit with another bill later. Don't make my mistake!
NebulaNomad
ā¢OMG thank you for mentioning this! I just checked my pay stubs and they ARE withholding state taxes, but I hadn't even thought to check. That's at least one relief in this mess.
Another option to consider - you might qualify for an Offer in Compromise if you truly can't pay the full amount. The IRS will sometimes settle for less than what you owe if you can prove financial hardship. Their pre-qualifier tool on the IRS website can help you determine if you're eligible.
This is terrible advice for this situation. Offers in Compromise are extremely difficult to qualify for and usually only apply when someone has no hope of ever paying the full amount due to permanent financial hardship. With an $85k salary, OP almost certainly wouldn't qualify. An installment plan is much more appropriate.
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Paolo Romano
H&R Block employee here (not corporate, just a seasonal preparer). I want to apologize for your experience - it's not how things should work. Unfortunately, there's massive variation in quality between offices since many are franchises. Some tips for others: 1. Always ask for credentials. Some preparers have minimal training. 2. Get EVERYTHING in writing - including price quotes. 3. Request they contact you immediately for any rejections. 4. Never sign Form 8879 (e-file authorization) until you've reviewed everything. 5. Remember tax prep is a service industry - demand better service!
Thanks for the insider perspective. I'm curious - what causes such a dramatic change in refund amount after a rejection? Is it usually errors in the original filing or something else? And what should I have asked for specifically to prevent the huge price jump?
Paolo Romano
ā¢Dramatic refund changes after rejection usually happen when the preparer has to correct information that was entered incorrectly the first time. Common examples include incorrect filing status, missing income that the IRS already has on record (like a forgotten W-2 or 1099), or incorrectly claiming credits you don't qualify for. When these corrections happen, tax liability can shift dramatically. To prevent price jumps, always ask for a detailed price list before starting. Request a written breakdown of exactly what forms and schedules are included in the quoted price and what will trigger additional charges. Some offices charge per form rather than a flat fee, so things like reporting cryptocurrency transactions, self-employment income, or education credits can each add $50+ to your bill without warning. Get the pricing structure in writing and ask them to notify you before preparing any forms that would increase your originally quoted price.
Amina Diop
Did you sign something called an 8879 form? That's the e-file authorization. If they refiled without you signing a new one, that's a serious violation of IRS rules. They literally cannot legally submit your return without your signature on that form for each submission.
This is absolutely correct. I work at a different tax firm and we CANNOT submit without a signed 8879 for each filing. It's a huge compliance issue and could get them in real trouble with the IRS. The practitioner risks losing their filing privileges.
Olivia Garcia
Don't forget about QBI (Qualified Business Income) deduction for rental properties! If your income is below $170,050 (single) or $340,100 (married filing jointly) for 2025, you might qualify for an additional 20% deduction on your rental income after expenses but before depreciation. This could further reduce your tax burden. Just make sure your rental activity qualifies as a business and not just an investment for QBI purposes.
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Margot Quinn
ā¢Wait, I didn't know rental income could qualify for QBI. Does my rental automatically count as a business, or do I need to do something specific to qualify? Is there a minimum number of hours I need to spend managing it?
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Olivia Garcia
ā¢Rental property doesn't automatically qualify for QBI. The IRS has a "safe harbor" rule that requires you to maintain separate books and records for each property, spend at least 250 hours per year on rental activities (property management time counts), and keep contemporaneous records of time, dates, and services performed. If you use a property management company, you'll need to carefully document any additional time you spend on rental activities. Another option is to qualify as a "real estate professional" for tax purposes, but that requires 750+ hours annually in real estate activities. If your property doesn't meet the safe harbor requirements, you might still qualify under general business principles, but that gets more complicated.
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Noah Lee
Quick tip - make sure you're tracking all your startup expenses separately! When you convert your personal home to a rental, things like advertising costs, credit check fees, legal fees for creating a lease, etc. are all deductible. But the timing matters! Some expenses can be deducted immediately, others have to be depreciated over time. This makes a huge difference in your first year tax situation.
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Ava Hernandez
ā¢Would repairs done before renting out the property count as startup expenses or improvements? I'm about to rent my house and need to fix some things first.
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