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Daniel White
Just to add to the capital gains discussion - don't forget about state taxes too! The federal capital gains rate might be 15%, but depending on what state your in-laws live in, they could owe state taxes on top of that. Some states tax capital gains at the same rate as ordinary income. For example, I sold a vacation property in California last year and had to pay an additional 9.3% to the state on top of the federal capital gains tax. Made a big difference in my final numbers.
Gianna Scott
ā¢Oh man, I didn't even think about state taxes! They're in Pennsylvania - any idea what the rate would be there?
Daniel White
ā¢Pennsylvania has a flat income tax rate of 3.07% that applies to capital gains too. So your in-laws would pay that on top of the federal 15%. It's lower than many states, but still adds up. Make sure they account for both state and federal taxes in their calculations. There's no special capital gains rate in PA - it's just treated as ordinary income at the state level. They'll need to report it on both their federal and state tax returns next year.
Nolan Carter
I'm seeing some confusion about cost basis here. Remember that in addition to the purchase price and documented improvements, your in-laws can also add certain closing costs from when they purchased the property to their basis. This includes: - Title insurance - Legal fees - Recording fees - Survey costs - Transfer or stamp taxes Also, when they sell, they can deduct selling expenses like real estate commissions, legal fees, and other closing costs directly from the sales price before calculating gain.
Wait that's super helpful! I sold my cabin last year and my accountant never mentioned adding the original closing costs to my basis. Can I still amend my return from last year to include those?
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Has anyone successfully used H&R Block software for this AMT credit carryforward situation? My company just granted more ISOs and I'm trying to figure out which software handles this best.
Mason Davis
ā¢I used H&R Block last year for my ISO/AMT situation and it worked fine. Form 8801 is available in their Premium version. The interface isn't as intuitive as some others, but it gets the job done. One tip: make sure you have your previous year's Form 6251 handy when you're working on 8801.
Thanks, that's really helpful! I'll stick with H&R Block then. Do you remember approximately where in the interface the AMT credit form was located? Just want to make sure I don't miss it.
One strategy that helped me deal with AMT from ISOs: If you're expecting to be in AMT for several consecutive years, consider exercising and holding ISOs in the HIGHEST AMT year, then doing disqualifying dispositions (immediately selling) in other years. This maximizes the value of your AMT credits when you can finally use them. For your specific question about TurboTax vs TaxSlayer - I've used both, and TurboTax Premier definitely does support Form 8801, it's just not obvious. TaxSlayer's interface makes it a bit easier to find the AMT credit forms in my experience. Also don't forget that keeping perfect records is crucial. Document every ISO transaction, your basis calculations, and keep copies of all AMT-related forms (6251, 8801) from every year. You might need these records for a decade or more until you finally use all your credits!
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Aisha Khan
Has anyone considered the possible relationship implications here? My ex used to deposit money in my account when I was between jobs and it created this weird power dynamic where I felt like I couldn't make independent decisions. Just something to think about - maybe set up a system where there's more transparency about the arrangement?
That's actually a really good point that I hadn't considered. We've been together for three years and have talked openly about finances, but I don't want her to feel like she's losing her independence. Maybe we should establish a more formal agreement about expectations during this period. Do you have any specific suggestions for how to structure this kind of temporary support without creating weird dynamics?
Aisha Khan
ā¢In my experience, having a specific timeframe and budget helps a lot. Maybe sit down together and create a temporary "support plan" with an end date or specific milestone (like when she finds a new job). For the actual mechanics, consider a joint account specifically for shared expenses that you both have access to, rather than just depositing into her personal account. That way it feels more like a shared resource than "your money." And definitely have regular check-ins about how you both feel about the arrangement - these things can create resentment if not discussed openly.
Ethan Taylor
One thing nobody's mentioned - if you're self-employed, are you properly documenting these cash withdrawals in your business accounting? The IRS might question large regular cash withdrawals from a business account if they don't align with your reported business expenses. Make sure you're clearly separating personal draws from business expenses!
Yuki Ito
ā¢This is a really important point. I'm a bookkeeper and I've seen self-employed clients get in trouble for poor cash withdrawal documentation. Make sure you're recording these as owner's draws or distributions, not as business expenses!
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Tyrone Hill
Have you looked into whether your state has any paid family leave programs? Some states offer short-term disability or family leave insurance that can provide partial income during maternity leave. Even in states without dedicated programs, you might qualify for temporary disability benefits for the recovery period after childbirth (usually 6-8 weeks). Also, make sure you understand your FMLA rights. If your company has at least 50 employees, you're entitled to 12 weeks of unpaid leave with job protection. Though with only 12 employees, your company might be too small to qualify.
Harmony Love
ā¢Thanks for this suggestion! Unfortunately my state doesn't have paid family leave, and my company is definitely too small for FMLA (we only have 12 employees). I did check into short-term disability but was told I would have needed to enroll before becoming pregnant. It's frustrating how few options there are for maternity leave in small businesses.
Tyrone Hill
ā¢That's really tough. Another option might be to negotiate a flexible arrangement with your employer that doesn't involve unemployment fraud. Maybe you could work reduced hours remotely during part of your leave, use any accumulated PTO, or spread a reduced salary over a longer period. Many small businesses work out these kinds of arrangements. Remember that while what they're suggesting might seem helpful, they're asking you to take all the risk. If unemployment investigates (which they often do), you'd be the one who filled out a fraudulent application, not your employer.
Omg I have been through this EXACT thing! My boss suggested the same "unemployment trick" with my maternity leave last year. I almost went along with it bc I was desperate for income during my leave. Thank goodness I talked to my uncle who works in HR first! He explained that this is 100% fraud and I could end up having to repay all benefits plus penalties, get disqualified from future unemployment when I might really need it, and potentially even face criminal charges in extreme cases.
What did you end up doing instead? I'm in a similar situation now and feel stuck between no income or doing something that might be illegal.
Anthony Young
One thing no one's mentioned yet - if you're worried about owing again next year, you can also make estimated quarterly tax payments for your freelance work. That's what I do to avoid a big bill at tax time. The due dates are April 15, June 15, September 15, and January 15 (for the previous year's last quarter).
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Evan Kalinowski
ā¢Do you just calculate 25% of what you think you'll owe for the year and pay that each quarter? Or is there some special form you need to fill out? This might be a good solution for me.
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Anthony Young
ā¢It's a bit more nuanced than just 25% each quarter. You can use Form 1040-ES which has a worksheet to help you estimate what you'll owe. Alternatively, you can base it on what you owed last year (which is the "safe harbor" approach to avoid underpayment penalties). The payments aren't perfectly even either - they're based on income during specific periods. The IRS website has a direct pay option that makes it pretty easy once you know your amount. Just select "estimated tax" as the payment reason. It's definitely worth doing if you have significant untaxed income!
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Charlotte White
What tax software are ppl using these days? I've been using TurboTax but I swear they jack up their prices every year, and I'm wondering if there are better options for handling freelance + regular w2 income.
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Admin_Masters
ā¢I switched to FreeTaxUSA last year and it was WAY cheaper than TurboTax. Handled my W-2 and 1099 income just fine. Federal filing is free and state was like $15. The interface isn't as pretty but it gets the job done.
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