One thing I haven't seen mentioned yet is the timing consideration for your coaching business. Since you're relocating in a few months, you might want to factor in when you'll actually need the tax deduction. If you're having a particularly high-income year, the charitable deduction might be more valuable this tax year. But if you're expecting lower income due to the relocation disruption, you might benefit more from the immediate cash from selling. Also, don't forget about the moving expense implications. If you're moving for business reasons, some of your relocation costs might be deductible, which could affect your overall tax strategy. Given that you fully expensed everything under Section 179 in 2022 (making any sale proceeds ordinary income), I'd lean toward donation unless you desperately need the cash flow right now. The tax benefit will likely be better than paying taxes on whatever you'd get from selling 3-year-old furniture.

This is a great question that many home-based business owners face! Based on the discussion here, it sounds like your Section 179 expensing in 2022 is the key factor that changes everything. Since you fully expensed the furniture already, selling would mean reporting the entire sale amount as ordinary income, which at your 24% tax bracket could eat up a significant portion of what you'd receive. For donation valuation, I'd suggest taking detailed photos of each piece and researching comparable used items on Facebook Marketplace, OfferUp, and similar platforms to establish fair market value. Document everything thoroughly - the IRS likes to see that you made a good faith effort to determine reasonable values. One practical tip: consider a hybrid approach. If any pieces are in particularly good condition and likely to sell quickly for a decent price, maybe sell those. For the items that would be harder to sell or wouldn't fetch much, donation might be the better route. The small conference table and chairs, for example, can be tricky to sell but might have good donation value. Also remember that donation gives you more predictable timing - you know exactly when it happens and can plan the tax benefit accordingly, whereas selling might drag on for months with no guarantee of success.

I think everyone's missing an important point here. If you're doing a W2 job, you CANNOT take the home office deduction anymore after the Tax Cuts and Jobs Act! Only self-employed people can take it now.

Great question about the garage conversion! I want to add a few additional considerations that might be helpful: Since you're meeting clients in this space, make sure you're documenting the business meetings. Keep a log of client visits, business calls, and any other business activities conducted in the garage office. This helps establish the "regular use" requirement beyond just the "exclusive use." Also, consider the timing of when you can start claiming the deduction. You can only deduct expenses from the date the space was "placed in service" for business use - so if you finished the conversion in March but didn't start using it for business until April, your deduction would be prorated. One thing to watch out for: if your side business operates at a loss, the home office deduction can't create or increase that loss. The deduction is limited to the income from the business activity conducted in the home office. Finally, since you mentioned this is an attached garage, make sure there's proper separation from your main house if you're claiming it as a separate structure. The IRS looks at whether the office space is an integral part of your home or a separate structure, which can affect how certain expenses are calculated. Keep excellent records of everything - the conversion costs, ongoing maintenance, and business use documentation. Good luck with your tax planning!

Can you request a waiver for the penalty if you had a good reason for underpaying? I had a medical emergency last year that drained my savings, so I couldn't make my Q4 payment on time.

The $265 penalty on $27K owed actually makes sense when you understand the calculation. The penalty isn't based on your total tax owed, but on the quarterly underpayments throughout the year. Here's what likely happened: If most of your consulting income came later in the year (Q3 or Q4), you only had penalties on the quarters where you were actually short. The IRS uses Form 2210 to calculate this - they look at each quarter separately and only penalize the periods where you didn't pay enough. The penalty rate for 2023 was around 7-8% annually, but it's only applied to the specific quarterly shortfalls. So if you were only short in Q4, you'd only pay penalties on that quarter's underpayment, not the full year. For 2024 going forward, consider making estimated payments equal to 100% of your 2023 total tax liability (110% if your AGI was over $150K). This "safe harbor" rule protects you from penalties even if you end up owing more. Much easier than trying to estimate variable consulting income!

Am I the only one who thinks the whole education credit system is ridiculously complicated? I went through 3 different tax software programs last year trying to figure out how to claim my education expenses correctly. Ultimately I found TurboTax handled this specific scenario better than HR Block or TaxAct. It gives you an option to say "My school did not provide a 1098-T" and then lets you manually enter your qualified expenses.

I had this exact same issue with HR Block last year! The software gets stuck in that loop where it keeps asking for the 2024 1098-T even when you tell it you don't have one. Here's what finally worked for me: Instead of following the education section's 1098-T pathway, I had to completely exit out of that section and look for "Education Credits" under a different menu (I think it was under "Deductions & Credits" rather than the main education flow). From there, I was able to manually enter my education expenses without the software expecting a specific form. You'll want to use the amounts from your 2023 1098-T since those were your actual qualified expenses - the fact that box 7 was checked means those payments were for your 2024 academic year. It's super frustrating that the software doesn't handle this common scenario better, but once you find the manual entry path it should work fine. You might also try clearing your browser cache and starting fresh if you've been going in circles for a while.

One thing nobody's mentioned - have you considered the character of the gain? If this was actively farmed land that you used in a trade or business and held for many years, it might qualify for Section 1231 treatment which could give you more favorable tax rates than regular capital gains.

This is exactly the kind of complex transaction where having proper documentation and expert guidance is crucial. From what I've read here, it sounds like CPA firm B is on the right track with the bargain sale treatment. One additional consideration - make sure you coordinate the timing of this transaction carefully. Since you're dealing with both capital gains and a substantial charitable deduction, you'll want to consider whether it makes sense to complete this in the current tax year or defer to next year based on your overall tax situation and AGI limitations for charitable deductions. Also, given the complexity and the contradictory advice you've received, you might want to consider getting a third opinion from a tax professional who specifically specializes in conservation transactions and bargain sales. The nuances around basis allocation, documentation requirements, and potential Section 1231 treatment (as mentioned above) really benefit from specialized expertise. The stakes are high enough here that the cost of getting it right the first time will likely be much less than dealing with IRS issues later if something is handled incorrectly.