This thread has been incredibly helpful! I'm in a very similar situation - I've been supporting my mom who lives in an assisted living facility about 30 minutes away. I pay $3,200 monthly for her care plus all her medical expenses and personal needs, while she only receives $1,800 in Social Security. I've been filing as Single for the past two years because I didn't realize the "living with you" rule had an exception for parents. After reading through all these responses, I'm confident I qualify for Head of Household status and have been missing out on significant tax savings. One thing I wanted to add for others in similar situations - make sure to factor in ALL the support you provide when calculating that 50% threshold. It's not just the big expenses like rent or facility fees. Things like clothing, personal care items, phone bills, cable/internet, transportation costs, and even recreational activities count toward support. I've been keeping track in a simple notebook, but I'm definitely going to switch to a spreadsheet system like others have suggested. It'll make tax time so much less stressful knowing I have everything documented properly. Thanks to everyone who shared their experiences - you've potentially saved me thousands in taxes I should have been claiming!

This is such a comprehensive discussion! I wanted to add one important point that hasn't been mentioned yet - if you're supporting a parent who lives separately, make sure to keep records of ANY rent or mortgage payments you make for their housing, even if it's not in your name. I support my grandmother who lives in her own apartment, and I pay her rent directly to the landlord each month ($1,400). Initially I was worried this wouldn't count the same as facility payments, but the IRS considers housing costs as support regardless of whether it's a private residence, assisted living, or nursing home. Also, for anyone wondering about the timing - you need to provide more than half the support for the ENTIRE tax year to claim Head of Household. So if you only started supporting your parent partway through the year, make sure your calculations cover just the period you were actually providing support, not the full year. The documentation advice everyone's given is spot-on. I use a simple Excel sheet with columns for Date, Amount, Category (rent, medical, food, etc.), and Payment Method. Takes maybe 5 minutes a month to update but gives me complete confidence when filing. One last tip - if your parent receives any government benefits like food stamps or Medicaid, those don't count as income that affects your ability to claim them as a dependent. Only consider their actual cash income like Social Security, pensions, or wages.

I went through this exact same situation last year with my SPX and SPY options trading! The confusion around Form 6781 is totally understandable - it's one of the more complex tax forms out there. One thing that really helped me was understanding the timing differences. For SPX options (Section 1256 contracts), you have to mark-to-market at year end even if you're still holding the positions. This means you'll report gains/losses on all your SPX positions in Part I whether you closed them or not. For SPY options that form straddles, you only report realized transactions in Part II, but you need to be careful about the loss deferral rules. If you realized a loss on one leg of a straddle while the offsetting position had unrecognized gains, you may have to defer some of that loss. I'd also suggest keeping very detailed records of when you opened and closed each position. The IRS can be pretty strict about the documentation for straddle transactions, especially if they audit. Make sure you can clearly show which positions were intended to offset each other and when those relationships were established. The good news is once you get through it the first time, subsequent years become much easier since you'll understand the process better!

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.

Just a practical consideration - if your vehicle is pretty old after 7 years of business use, consider if it's worth keeping for personal use at all. I was in a similar situation with a van I used for my plumbing business, facing about $18k in recapture. Instead, I sold it to one of my employees for its fair market value (about $7500) and still had to recapture, but at least I got some cash for it. Then I bought a different used vehicle for personal use that had never been a business asset. Worked out better tax-wise.

One thing that hasn't been mentioned yet is the timing of when you need to establish fair market value for the recapture calculation. The IRS requires you to determine the vehicle's FMV on the exact date you convert it from business to personal use, not when you file your taxes. I'd recommend getting a written appraisal from a qualified appraiser or at least documenting the value with resources like KBB, Edmunds, or NADA guides on the conversion date. Keep screenshots and print copies because you'll need this documentation if the IRS ever questions your recapture calculation. Also, don't forget that once you convert to personal use, you can no longer claim any business deductions for the vehicle - no more depreciation, repairs, insurance, etc. Make sure the timing works with your business needs before making the switch.

Has anyone considered using a 529 plan in this situation? If you're nervous about the market but want to avoid the capital gains hit, could you transfer the UTMA assets to a 529? I've heard this might be possible but not sure about the tax implications.

Something else to consider that might help with your timing decision - if your daughter will graduate in 2-3 years, you could potentially wait until after graduation when she's no longer a full-time student. Once she's not a student, the Kiddie tax rules won't apply even if she's under 24, assuming she's not living with you. This could give you more flexibility on when to realize the gains. However, you'd need to weigh this against your market risk concerns. If you're genuinely worried about a significant market downturn, the tax savings from waiting might not offset potential investment losses. Also, double-check whether your state has any additional considerations for UTMA accounts and capital gains. Some states have their own rules that could affect your decision timing.

Just a heads up from someone who works in software retail - the reason H&R Block limits downloads to one platform is purely a licensing/revenue issue. They want people with multiple computers on different platforms to pay twice. It's the same reason Adobe used to charge separately for Mac/Windows before they went subscription-based. You might want to consider TurboTax instead if cross-platform is important. I believe they allow you to download both Mac and Windows versions with a single purchase, though their software is generally more expensive than H&R Block. Another option is TaxSlayer which lets you install on multiple computers regardless of OS.

I actually ran into this same issue a few years ago and found a pretty simple solution that might work for you. Since you mentioned you're comfortable with dual-booting and using different operating systems, you could purchase the H&R Block software for whichever platform you use most frequently, then use a virtual machine to run the other version if needed. For example, if you buy the Windows version, you can run it natively when you boot into Windows on your main machine, and also run it in a Windows VM on your girlfriend's MacBook using something like Parallels or VMware Fusion. The performance is totally fine for tax software since it's not resource-intensive. This approach gives you the flexibility you want without having to deal with H&R Block's customer service or pay for multiple licenses. Plus, you'll have the exact same version and data files across both setups, which makes things consistent. I've been doing this for three years now and it works great - just make sure to keep your tax files synced between the systems using a cloud service or USB drive.