This is incorrect information. Property taxes cannot be added to your basis for inherited property. They're either deductible in the year paid (if you itemize) or not deductible at all. Only capital improvements can be added to basis.

Thanks for sharing your experience! That's encouraging to hear it went smoothly for you. Did your attorney try to argue that he was entitled to credit for teaching you the process or anything like that? I'm worried mine might try to claim I'm only able to do it myself because of his "expertise" he shared over the years.

Not at all! The agreement was for his services on a per-appeal basis, not for "teaching" me anything. It's like hiring a plumber - they don't get to claim a percentage of all future savings on your water bill just because you watched them fix your pipes. Property tax appeals are a standard process that anyone can learn. The forms and procedures are publicly available, and what constitutes a valid comparable property isn't some proprietary secret. Your attorney doesn't own the concept of property tax appeals. Just make sure you're not in the middle of an active appeal when you end things. Complete the current cycle, pay what you owe under your agreement, then notify him before the next cycle begins that you'll be handling it yourself going forward.

I used PropertyTaxLowerer.com last year and it was pretty good. Not free but WAY cheaper than giving up 50% to an attorney. They helped identify comps and filled out all the paperwork. I just had to sign and mail it.

Thank you for this advice! I definitely need to fix this for next year. How do I calculate how much to pay for quarterly estimated taxes? And where exactly on the W4 do I add extra withholding?

For estimated quarterly taxes, you can use the worksheet that comes with Form 1040-ES. Basically, you estimate your total tax liability for the year and divide by four. Pay special attention to your 1099 income - you generally need to set aside about 30-35% of that for taxes (15.3% for self-employment tax plus your income tax rate). For the W4, look at Step 4(c) "Extra withholding." You can put any additional amount you want withheld from each paycheck. If you have multiple W2 jobs, there's also a "Multiple Jobs Worksheet" that can help calculate this more precisely. Your HR department should be able to provide you with a new W4 form to update this information.

I amended last year and it was actually pretty easy. Just file Form 1040-X and include any updated forms that changed. FreeTaxUSA can help you prepare an amended return too. Just be aware that processing times are really slow right now - mine took about 4 months.

Is Form 3921 the same as the exercise confirmation that the company provides? My company gave me some PDF after I exercised but I'm not sure if that's the official form or if I should be looking for something else.

No, they're different documents. The exercise confirmation is generated by your company's equity management system when you complete the exercise transaction. Form 3921 is an official IRS form that employers are required to provide for ISO exercises. It should be titled "Exercise of an Incentive Stock Option Under Section 422(b)" at the top. If you haven't received Form 3921 by late January/early February, definitely ask your HR or stock administration team about it. Sometimes companies are late sending these out, but they're required to provide it for each ISO exercise transaction. The information on this form is what the IRS will use to verify your reporting, so it's crucial to have.

This is honestly the most underrated comment here. I got absolutely destroyed by AMT on my ISOs because I exercised about $200k worth of options (difference between FMV and strike) and ended up with a $55k tax bill with no cash to pay it. Had to sell some of my precious shares at a really bad time in the market just to cover the taxes.

Exactly - it's what financial advisors call the "phantom income" problem with ISOs. You're taxed on money you haven't actually received yet. For anyone reading this who's planning a large ISO exercise, consider doing a "cashless exercise and hold" for a small portion of your options. This means you exercise and immediately sell just enough shares to cover your potential tax liability, then hold the rest for long-term capital gains treatment. Yes, the shares you sell will be taxed at ordinary income rates, but it creates the cash to pay the AMT on the shares you're holding. Always better to plan ahead than be forced to sell at an inopportune time.

That's a good point! I hadn't even thought about the state tax angle. So I guess that's one benefit of living in Florida for tax purposes - not having to worry about an additional state tax return. Do most tax software programs automatically figure out whether you should itemize or take the standard deduction?

Most decent tax software will compare your potential itemized deductions against the standard deduction and recommend whichever gives you the better outcome. They'll run the calculations both ways and show you the difference. The better programs will also alert you if you're close to the threshold and might suggest ways to maximize deductions. Just be careful with the free versions of tax software - they sometimes don't include Schedule A (itemized deductions) and try to upsell you when you need it.

This bunching strategy is smart! I've done something similar with medical expenses. Had a bunch of elective procedures done in one year to cross that 7.5% AGI threshold. Got LASIK, dental work, and a couple other things I'd been putting off. Saved a decent amount overall.