I've been dealing with Form 6781 for options trading for a few years now, and I completely understand the initial confusion! One thing that helped me get organized was starting with the basic distinction between what goes where on the form. For your SPX options, these are Section 1256 contracts that go in Part I. The key advantage here is the 60/40 tax treatment (60% long-term, 40% short-term capital gains regardless of holding period). You'll report the net gain/loss from ALL your SPX trading for the year - both closed positions and mark-to-market adjustments on any positions still open at year-end. For SPY options, these are regular equity options. They only go on Form 6781 if they were part of actual straddle positions (meaning you had offsetting positions that substantially reduced risk). If they were just standalone option trades, they go on Schedule D like regular stock trades. The tricky part is identifying true straddles. Just because you traded both calls and puts doesn't automatically make it a straddle - the positions need to genuinely offset each other's risk. Look for situations where you held positions that would move in opposite directions under similar market conditions. I'd recommend starting by gathering all your year-end statements from your broker, as they often identify Section 1256 contracts separately. Then work through your SPY trades chronologically to spot any offsetting position pairs.

I've been following this thread with great interest as someone who just went through my first year of serious options trading! The advice about creating a detailed spreadsheet really resonated with me - I wish I had done that from the beginning. One thing I learned the hard way is to pay close attention to the wash sale rules when dealing with straddles. If you close a position at a loss and then establish a "substantially identical" position within 30 days, the wash sale rule can interact with straddle reporting in complex ways. This became an issue for me when I was rolling positions and didn't realize I was creating wash sales on top of straddle situations. Also, for anyone using multiple brokers (like I do for different strategies), make sure you're looking at positions across ALL your accounts when identifying straddles. I almost missed a straddle situation where I had SPY calls at one broker and SPY puts at another. The IRS doesn't care that they're at different firms - if the positions offset each other's risk, they can still constitute a straddle. The Form 6781 instructions are honestly pretty terrible for explaining real-world trading scenarios, so threads like this are incredibly valuable for understanding the practical application of these rules.

Great question about finding qualified cost segregation specialists! You'll want to look for professionals who are either engineers or have engineering backgrounds, often with credentials like PE (Professional Engineer) or designations from organizations like the American Society of Appraisers. Many are also CPAs with specific cost segregation training. The key is finding someone who understands both the engineering aspects (being able to properly classify building components) and the tax code requirements. They should be able to provide detailed engineering-based documentation that can withstand IRS scrutiny. Regarding audit experience - I went through an audit a few years back where cost segregation was questioned on a commercial property. The IRS was particularly interested in our methodology for separating personal property from real property. Having detailed engineering reports with photos, blueprints, and component-by-component analysis was crucial. The specialist we used had prepared everything with potential audit defense in mind, including detailed depreciation schedules and supporting calculations. For your roof coating situation, the documentation would likely focus on demonstrating which specific components (if any) serve functions separate from the basic building structure. The IRS generally accepts well-documented cost segregation studies from qualified professionals, but they want to see real engineering analysis, not just aggressive tax positions. Given the complexity and your $135k project size, this is definitely worth exploring with both your returning accountant and a cost segregation specialist.

This has been such a comprehensive discussion! As someone new to the community, I'm amazed by the depth of knowledge being shared here. I wanted to add one more perspective that might be relevant to the original poster's situation. Since you mentioned needing financial projections before your accountant returns, you might want to consider the impact of your state's tax treatment as well. Some states don't conform to federal bonus depreciation rules or have different QIP treatment, which could significantly affect your overall tax savings calculations. Also, given that this is an 8-year-old property that was already generating good income, you might want to model how this improvement affects your property's basis for future sale purposes. While accelerated depreciation provides great cash flow benefits now, it also increases your depreciation recapture exposure when you eventually sell. With real estate values generally trending upward, this could be a meaningful consideration for your long-term investment strategy. One practical suggestion: while waiting for your accountant, you could reach out to your coating contractor to get a detailed breakdown of the work performed. Having line-item costs for materials vs. labor vs. any additional components could be valuable whether you end up pursuing cost segregation or just need detailed documentation for your chosen depreciation method. The fact that you're thinking about this proactively rather than just defaulting to basic depreciation shows great attention to tax planning - that mindset will serve you well as you continue building your real estate portfolio!

Just be prepared for your ex to potentially file incorrectly anyway. My ex filed as married filing separately even though we were divorced by year-end and it caused my return to be rejected when I tried to e-file as single. It was a nightmare to fix. Maybe reach out to your ex proactively and explain the December 31st rule, or have your tax preparer do it. Might save you both a headache later.

This is such a common source of confusion! I went through almost the exact same situation two years ago. The key thing to remember is that the IRS doesn't care how long you were married to your ex during the year - only your marital status on December 31st matters for filing purposes. Since you were legally married to your new husband on December 31st, you can absolutely file jointly with him. Your ex will need to file as single, not married filing separately, because he was divorced on December 31st. The "married filing separately" status only applies to people who are actually married to each other on the last day of the tax year. I'd suggest getting this information directly from the IRS or a tax professional to share with your ex, since he seems confused about the rules. It might help avoid any filing errors that could cause problems for both of you later. Good luck!

Don't stress too much about perfect documentation here. I've been through this exact situation. Just estimate your income as accurately as possible on that substitute W-2 form. If you worked regular hours, it should be pretty easy to calculate (hours per week × hourly rate × weeks worked). Save any evidence you have (text messages about shifts, bank deposits, etc.) just in case, but in my experience, the IRS didn't question anything when I submitted my substitute form.

I went through something very similar when a small restaurant I worked at suddenly closed without giving anyone their W-2s. Here's what I learned from that experience: The Social Security Administration check is definitely your first step - if nothing shows up there, you know for certain they never reported your wages. Then Form 4852 is your best friend. Don't overthink the income estimation - just be as accurate as you can with the information you have. One thing I wish someone had told me earlier: keep detailed records of everything you're doing to resolve this situation. Write down when you tried to contact the employer, what steps you took to get your W-2, etc. The IRS really appreciates seeing that you made good faith efforts to get proper documentation before filing the substitute form. Also, don't forget that you'll probably owe both federal and state income taxes on this unreported income, plus potentially some penalties for underpayment since nothing was withheld. It's worth setting aside some money now so you're not caught off guard when you file. The important thing is that you're taking care of it properly rather than trying to hide it.

One thing to consider that hasn't been mentioned much is the depreciation savings. If you're currently driving your 2021 Honda Civic for personal use, you're putting wear and tear on your own asset. With a company car, all that depreciation hits their books instead of yours. I'd also ask your employer about their policy for different types of personal use. Some companies are more restrictive about things like out-of-state trips or using the car for ride-sharing/delivery services. And definitely find out if they have any mileage tracking requirements - some employers want detailed logs of business vs personal use, which can be a hassle. The maintenance aspect is huge too. If the company covers oil changes, tire replacements, repairs, etc., that's real money saved even after the tax hit. I'd estimate what you typically spend annually on your Honda's maintenance and factor that into your decision.

Great question about company car policies! Travel restrictions vary widely by employer. Some companies have no geographic limits as long as you're using it for approved personal use, while others restrict travel to certain states or within a specific radius from your home base. The key things to ask HR about: 1) Geographic restrictions (if any), 2) Whether you need pre-approval for long trips, 3) Who's responsible if something happens out of state, and 4) Whether their insurance coverage changes based on location. Most companies I've seen allow road trips as long as you're not using the car for business purposes like Uber or moving services. But definitely get this in writing - the last thing you want is to be stranded somewhere because you violated a policy you didn't know about. Also worth noting that longer trips will increase your personal use percentage, which affects your taxable benefit calculation. So factor that into your overall cost analysis when deciding if the company car makes financial sense for your situation.