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One strategy that's worked well for me in transitioning from high-income to wealth building is real estate investing through Delaware Statutory Trusts (DSTs). They're classified as 1031 exchange eligible, and when structured properly, can provide both significant tax deferral and decent cash flow. I was able to sell some highly appreciated property and instead of paying capital gains, rolled the proceeds into a DST. Now I get monthly distributions that have much more favorable tax treatment than my W-2 income due to depreciation pass-through. The key is finding DSTs with quality properties and experienced management. This approach has helped me gradually shift my tax profile from someone paying the highest marginal rates on earned income to someone building wealth through tax-advantaged structures.
I've heard about DSTs but don't really understand how they're different from REITs? Are there minimum investment requirements? My financial advisor never mentioned these as an option.
DSTs are fundamentally different from REITs in both structure and tax treatment. Unlike REITs which are securities, DSTs are considered direct ownership in real estate for tax purposes, which qualifies them for 1031 exchanges. This means you can defer capital gains taxes by rolling proceeds from property sales into DSTs. Minimums typically start around $100,000, which is higher than REITs, but that's because they're designed for accredited investors. The tax benefits are substantial - you'll receive K-1s showing your portion of depreciation, which often shelters a significant portion of the cash distributions from immediate taxation. Many financial advisors aren't familiar with them because they require specialized knowledge and typically don't fit into standard model portfolios. You'll want to work with someone who specializes in tax-advantaged real estate strategies for high-income professionals.
Has anyone here looked into Opportunity Zone investments? My tax attorney mentioned them as a way to defer capital gains taxes from some stock I sold last year. Apparently you can roll the gains into designated "opportunity zone" projects and defer taxes until 2026, plus eliminate taxes on any appreciation of the new investment if held for 10 years. Sounds too good to be true?
I've invested in two Opportunity Zone funds. They do work as advertised tax-wise but be extremely careful about the underlying investments. Many OZ areas are economically distressed for good reason, and some developers are creating poor investments that only make sense because of the tax benefits. The best approach is to find OZ investments that would make sense even without the tax advantages. I found a multi-family development in an emerging area just outside a major city that had strong fundamentals regardless of the OZ benefits. The tax deferral and eventual exclusion is just a bonus.
That's really helpful insight. I was looking at a fund that invests in multiple OZ projects to spread the risk, but you're right that I should be evaluating the underlying economics first. What documentation do you need for tax purposes? My accountant mentioned something about attaching an election statement to my return and filing Form 8997 annually, but I want to make sure I don't miss anything that could jeopardize the tax benefits.
Something nobody's mentioned yet is the business-use percentage. If you're using this van even 10% for personal use, that affects everything. You can only claim the business portion of either method. With standard mileage, you just count business miles. With actual expenses/179, you have to calculate the business-use percentage and can only deduct that portion of expenses and depreciation. IRS is super picky about this during audits!
Do you have to track personal miles separately? Or just know the total miles driven in a year and subtract business miles from that?
You need to track both. The IRS wants to see your total miles for the year (odometer readings) and your business miles specifically. The difference is your personal miles. They want documentation showing how you tracked this. Most audits of vehicle deductions focus on inadequate mileage logs. I recommend using a mileage tracking app that automatically logs your trips - much easier than trying to reconstruct it later.
I'm in construction and use a similar vehicle. My accountant told me to really think about future years. If you plan to put this many miles on the vehicle consistently (40k+ per year), the standard mileage rate often wins in the long run, especially with gas prices these days. Section 179 gives you a big deduction now but smaller ones later. Standard mileage keeps giving if you drive a lot.
Thanks for sharing your experience. I do expect to maintain high mileage (40-45k) annually for at least the next 3-4 years based on my current clients and service area. I'm leaning toward the standard mileage based on everyone's advice, especially since it seems to provide more flexibility if my situation changes.
Don't forget to check if your home country has a tax treaty with the US! This can significantly impact how your LLC income is taxed. I'm from the UK with a similar setup, and certain types of business income are taxed differently because of the US-UK tax treaty. Also, make sure you're tracking your physical presence in the US carefully - the substantial presence test is based on a weighted formula (all days in current year + 1/3 of days in previous year + 1/6 of days from year before that). This determines whether you file as a resident (1040) or non-resident (1040NR).
Thanks for this reminder about the tax treaty! I'm from Singapore and I believe there is a tax treaty. Do you know if I need to file any special forms to claim tax treaty benefits? And how exactly do I track my physical presence - is there an official way to document this?
You would need to file Form 8833 to claim tax treaty benefits. This form reports treaty-based positions that affect your tax liability. For Singapore specifically, the treaty has provisions covering business profits, but you need to determine if your income qualifies under the permanent establishment rules. For tracking physical presence, I recommend keeping a detailed log of all your international travel. Save boarding passes, entry/exit stamps in your passport, and any other travel documentation. The IRS doesn't provide an official tracking method, but during an audit, they may ask for proof of your whereabouts. Some people use apps like TravelTracker or Taxday to help with this. The important thing is to have documentation of every day you were outside the US.
Another thing to consider - your Texas LLC might not have state income tax, but you might still have filing requirements depending on your business activities! Don't forget about franchise tax or public information reports that might be required even without income tax. Also, does your home country recognize the US LLC structure? Some countries will treat it as a corporation instead of a pass-through entity, which could create mismatched taxation. I learned this the hard way!
This is a really important point. I have a Delaware LLC but live in California, and I got hit with a surprise $800 minimum franchise tax my first year because I didn't understand the state requirements were different. OP should definitely check Texas requirements even though they don't have state income tax.
Has anyone tried using their phone to record the conversation during these business meals instead of taking notes? Seems like it would be easier and more thorough.
Be careful with recording conversations! Depending on your state, you might need the other person's consent to record them. Some states require both parties to consent to being recorded.
Good point, hadn't thought about the legal issues with recording. I'll stick with taking notes after the meeting.
Something else to consider - if you're still incorporating the charity, these might be startup costs rather than regular business expenses. The IRS allows you to deduct up to $5,000 in startup costs in your first year of business, with the rest amortized over 15 years. But the meal would still be subject to the 50% limitation within that startup cost category.
That's a really good point I hadn't considered. So I should be tracking these early expenses separately as startup costs? Does that change what documentation I need to keep?
Yes, definitely track these early expenses separately as startup costs. The documentation requirements are the same (receipt, who you met with, business purpose), but the way you'll claim them on your tax forms will be different. Keep a clear record showing these expenses were incurred before your official launch date. This helps establish that they're truly startup costs. Once your charity is fully incorporated and operational, you'll want to have a clean break in your accounting to show when regular operational expenses began. This distinction can be important if you're ever audited.
QuantumQuasar
From my experience as a small commercial property owner, you ABSOLUTELY need to be depreciating the building. Here's what my CPA told me: When you sell a commercial property, the IRS assumes you've taken all allowable depreciation WHETHER YOU ACTUALLY DID OR NOT. So if you haven't been claiming it, you're essentially paying taxes on money you could have saved. I suggest working with a qualified tax professional to determine a reasonable allocation between land and building (maybe 75/25 in your unusual case) and file amended returns. Yes, it's a pain, but it's better than leaving money on the table or having issues when you sell.
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Luca Romano
ā¢Thanks for the feedback. So even with the weird situation where the land appraisal was higher than my total purchase price, I still need to allocate some value to the building? Would I need to get another appraisal specifically breaking down the components, or can I just make a reasonable allocation myself?
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QuantumQuasar
ā¢Yes, you definitely still need to allocate some value to the building. The IRS won't accept that a functional commercial building has zero value, regardless of the land appraisal. You don't necessarily need a new formal appraisal, but you should have some reasonable basis for your allocation. I'd recommend looking at the county tax assessment to see how they split land vs. improvements, or checking comparable properties in your area. Many CPAs recommend documenting your methodology in case of questions later. A 75/25 or 80/20 land-to-building split might be reasonable in your case, but have documentation to back it up.
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Zoe Papanikolaou
Don't forget about potential recapture tax! When you sell a commercial property, you'll pay a 25% tax on all the depreciation you've claimed (or SHOULD HAVE claimed) over the years. So if you haven't been depreciating the building but should have been, you'll still face that tax liability when you sell. Also, check with your accountant about cost segregation - you might be able to accelerate depreciation on certain components of the building beyond just the standard 39-year schedule.
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Jamal Wilson
ā¢So you're saying the IRS will tax you on depreciation you SHOULD HAVE taken even if you didn't actually get the tax benefit? That seems incredibly unfair. Is there any way around this if OP sells soon?
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