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Another option I haven't seen mentioned yet is using a 1031 exchange for real estate investments. If you own investment property and want to sell, you can defer capital gains taxes by reinvesting the proceeds into a similar property. It's not eliminating the tax, but it's kicking the can down the road which can be valuable. Also, if you're planning to sell a business, look into Qualified Small Business Stock exemptions. If you meet certain requirements, you might exclude up to 100% of the gain from federal tax. For monitoring and planning, I've found Personal Capital's free tools pretty decent for basic capital gains tracking across accounts.
Is there something similar to 1031 exchanges but for stocks? Like if I wanted to sell my Amazon shares and buy Google instead, is there any way to defer the capital gains?
Unfortunately, there isn't a direct equivalent to 1031 exchanges for stocks. Those tax-deferred exchanges are specifically for real estate and certain types of personal property, but not securities like stocks or bonds. When you sell stocks, even if you immediately reinvest the money in different stocks, you'll generally have to pay capital gains tax on any profit. The closest option for stocks would be to do your investing within tax-advantaged accounts like IRAs or 401(k)s where you can buy and sell without triggering immediate tax consequences, but that doesn't help for investments you already hold in taxable accounts.
Has anybody tried cost basis management across accounts? I started doing this last year and it reduced my capital gains significantly.
I've been doing this for my clients for years. The key is tracking specific tax lots meticulously and choosing which ones to sell based on your current year tax situation. Some brokerages make this easy with their cost basis settings (specific identification method instead of FIFO). Just make sure you're consistent with your approach.
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Dont forget Guidestar (now called Candid) for nonprofit financials! https://www.guidestar.org/ You can see complete Form 990s there which includes revenue, assets, and even what they pay their executives. Lot of real estate held by religious orgs, educational institutions and foundations. Also for publicly traded REITs (Real Estate Investment Trusts), use any investment site like Yahoo Finance to see their financials. Most big commercial property owners are publicly traded.
Thanks! Do you know if Guidestar shows smaller local nonprofits too? Like if there's a local community development corporation that owns buildings in my town, would they show up there?
Yes, Guidestar/Candid includes even small local nonprofits as long as they've filed their Form 990s with the IRS. Community Development Corporations (CDCs) are typically registered nonprofits that must file, so you should find them there. The basic search is free, though they have tiered subscriptions for more detailed info. Even the free level should show you basic financial data and confirm if a local CDC owns specific properties. Just search by the organization name or EIN if you have it.
I work for a title company and honestly? The best source nobody mentions is just your local GIS (Geographic Information System) website. Most counties have these now - just google "[your county name] GIS" or "[your county] property search" and you can usually search by address. It wont show income but does show: - Current owner name - Previous sale prices and dates - Tax assessments - Property details - Sometimes even links to deed documents For who ACTUALLY owns it (beyond the LLC) try searching the LLC name in your state's business entity search (usually Secretary of State website).
This is super helpful! I just tried my county's GIS and was surprised how much info is there. Question though - I found an LLC that owns several properties, but when I looked it up on my state's business search, it just shows another LLC as the owner. Is there a way to break through this LLC nesting doll situation?
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5 One important thing nobody's mentioned yet is the Substantial Presence Test and potential tax treaty benefits. Even without a specific tax treaty, your father might benefit from filing Form 8833 (Treaty-Based Return Position Disclosure) if there's any applicable international agreement between the US and his country. Also, if he maintained a tax home in the Middle East and was physically present there for at least 330 days, he might qualify for the Foreign Earned Income Exclusion, which could exclude over $100,000 of foreign earnings from US taxation. But be careful - retirement income and investment income typically don't qualify as "earned income" for this exclusion.
3 I thought the Substantial Presence Test only applies to determining if someone is a resident alien or not? Doesn't having a green card automatically make you a resident alien regardless of physical presence?
5 You're absolutely right - I should have been more precise. Green card holders are automatically considered resident aliens for tax purposes regardless of physical presence, so the Substantial Presence Test isn't relevant in this case. My main point about the Foreign Earned Income Exclusion still applies though. Even without a specific tax treaty, there are provisions that could help reduce his US tax liability on foreign income. However, you're correct that retirement income typically doesn't qualify as "earned income" for the FEIE since it wasn't actively earned during the tax year.
22 Does your father own any property or investments back in his home country? That's another important consideration. If he owns rental property or has investment accounts there, he'll need to report that income too. And depending on the total value, there may be additional reporting requirements beyond just the income. Foreign mutual funds are especially complicated because they're often classified as PFICs (Passive Foreign Investment Companies) which have special reporting requirements on Form 8621 and can be taxed at higher rates.
1 He does have a small apartment that he rents out occasionally and some local investment funds through his bank there. I had no idea about these PFIC rules - that sounds really complicated. Is there a value threshold for when you need to report these foreign investments?
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I pay my teenage kids in my business (I own a retail shop) but I actually have them work - stocking inventory, helping with social media, etc. For really young kids like yours, the image rights approach can work but be SUPER careful with documentation. Make sure you: 1) Have a formal contract for the image rights 2) Pay market rates (research what others pay for similar usage) 3) Document EVERYTHING - when photos are taken, where they're used, etc. 4) Keep the money in accounts in their names Also consider setting up Roth IRAs for them with this earned income - amazing long-term tax benefits!
Doesn't the IRS get suspicious when they see really young kids getting paid? My accountant warned me that paying anyone under 7 would be a red flag.
The age itself isn't necessarily the red flag - it's whether the arrangement seems legitimate and reasonable. Many child actors and models are extremely young. The key is that you're paying for something with clear business value (the right to use their images in your marketing) and documenting the business purpose. Your accountant is right to be cautious though. The IRS does scrutinize family employment arrangements. That's why documentation is crucial - you need contracts, proof the images are actually used in your business, and evidence that the compensation is reasonable compared to market rates. Start modest with the amounts and keep everything professional and well-documented.
Just wanted to add another approach - we pay our kids (ages 6-11) as models for our home-based business that sells children's products. Instead of buying "image rights," we pay them as independent contractors for specific photoshoots. We complete W-9s, issue 1099s, and track hours/shoots carefully. We also worked with an attorney to draft simple model release forms and contracts. We pay about $100-150 per photoshoot which happens 2-3 times monthly. Pictures go directly to our product listings and social media marketing.
This sounds more legitimate than just "buying image rights." Have you ever been audited on this? I'm worried about getting flagged.
Santiago Diaz
One thing nobody's mentioned yet - make sure you're measuring your space correctly! I made the mistake of just eyeballing my office area and saying "yeah that's about 15% of my apartment" which led to problems during an audit. Get a measuring tape and actually measure the square footage of your workspace versus the total living space. And take photos of your dedicated workspace to show it's actually set up as an office. The IRS is pretty strict about the "exclusive use" requirement - if you've got a TV and game console in there too, you might be in trouble.
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Millie Long
•Do you need to include closets and bathrooms in the total square footage calculation? My apartment is about 800 sq ft total, but my office is 100 sq ft. But there's also 80 sq ft of closet space and a 70 sq ft bathroom. Not sure if those count toward the total or not.
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Santiago Diaz
•You should include the entire square footage of your apartment when calculating the percentage. This includes closets, bathrooms, hallways - everything. So in your case, you would use the full 800 sq ft as your denominator in the calculation. So if your office is 100 sq ft of an 800 sq ft apartment, your business use percentage would be 12.5% (100 ÷ 800), not the higher percentage you'd get if you excluded some areas. The IRS wants you to use the total square footage of your home, not just the "livable" areas. Make sure you document your measurements carefully!
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KaiEsmeralda
Just a warning about this deduction - it can potentially trigger an audit flag, especially if you're deducting a large percentage of your rent. When I claimed 30% of my apartment as a home office (legitimately - I run a full-time business from home), I got audited the following year. Make sure your documentation is solid. In my case, I had a floor plan with measurements, photos of my workspace, utility bills showing increased usage during business hours, and a dedicated business phone line. Still got audited, but was able to defend everything successfully.
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Debra Bai
•happened to me too! claimed about 25% of my townhouse for my consulting business and got a letter from the irs 8 months later. such a headache even tho everything was legit. they wanted bank statements, photos, client invoices from my home address, everything!!! took like 3 months to resolve.
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