Just wondering - does anyone know if using TurboTax or another DIY software is reasonable for filing trust returns? My family is in a similar situation and we're trying to save on preparation fees.

I've been dealing with trust taxation for several years now, and I'd strongly recommend getting clarity on whether this is actually a grantor trust or a non-grantor trust before making any filing decisions. The fact that it was created when your dad's mom passed away suggests it might be an inherited irrevocable trust, which would typically be a non-grantor trust requiring its own Form 1041 filing. If it IS a grantor trust, then yes, everything flows to your dad's personal return regardless of whether you file a separate informational return. But if it's a non-grantor trust (more likely given the circumstances), then it must file separately and the trust itself pays taxes on retained income. The potential tax savings your dad's preparer mentioned could make more sense in a non-grantor trust scenario, where the trust can deduct administrative expenses against its own income. I'd suggest having the attorney review the trust document to confirm the grantor status before proceeding with any filing strategy.

Something else to consider - if the stock price drops after your purchase and you sell at a loss, you might face the wash sale rule complications if you continue participating in the ESPP program. This has bitten me before when I sold some underwater ESPP shares but then acquired more through the next purchase period within 30 days.

Great point about the wash sale rule complications! This is something that caught me off guard when I first started with ESPPs. The automatic nature of ESPP purchases makes it really easy to accidentally trigger wash sale rules if you're trying to harvest losses from previous purchases. One strategy I've learned is to be very strategic about timing any ESPP share sales if you're planning to continue in the program. You either need to wait more than 30 days after selling before your next ESPP purchase, or suspend participation for a purchase period if you want to realize losses for tax purposes. The wash sale rule gets even more complex with ESPPs because you might have shares from multiple purchase dates with different cost bases. I keep a spreadsheet tracking all my ESPP purchases and any sales to avoid accidentally creating wash sale situations. It's tedious but has saved me from some nasty surprises at tax time. Also worth noting - if you have other employee stock options or restricted stock that vest around the same time, those can potentially trigger wash sale rules too if they're the same underlying stock.

One thing nobody has mentioned yet is that if you're putting a brokerage account in an LLC, make sure your broker even allows it! I tried to do this with Fidelity last year and had a nightmare of an experience. They required all sorts of additional paperwork, and ultimately I had to open a specialized account type. Also, be aware that some brokers will charge higher fees for LLC accounts compared to individual accounts. And some trading platforms have different terms of service for entity accounts vs. individual accounts.

Just a heads up - don't forget that putting your brokerage account in an LLC means you'll need to get an EIN from the IRS, even though it's a disregarded entity for tax purposes. Your broker will require it. Also, for maximum asset protection, make sure you don't commingle personal and LLC funds. Have a separate bank account for the LLC and keep good records. The whole "corporate veil" protection can be pierced if you don't respect the separation between your personal finances and the LLC's.

just wanna add something nobody's mentioned yet - if ur using schedule C as a self employed hairdresser, don't forget that writing off too many unusual deductions can increase ur chances of an audit. massage deductions might raise flags if they're large compared to ur income.

As someone who's dealt with similar work-related health issues, I'd strongly recommend getting that documentation from your chiropractor as others have mentioned. The key is establishing a clear medical connection between your work duties and the need for treatment. One thing I haven't seen mentioned yet - you might want to keep a simple log of how the massages specifically help your work performance. Note things like "reduced shoulder pain allowed me to work full 8-hour shift without breaks" or "improved grip strength after treatment." This kind of documentation can strengthen your case that these aren't just general wellness expenses. Also, $2,600 for bi-weekly massages seems reasonable for medical necessity, but make sure you're not mixing in any purely relaxation sessions. Only the therapeutic treatments that directly address your work-related strain would qualify. Have you considered whether your employer might cover some of these costs as a workplace injury prevention measure? Some salons will reimburse ergonomic supports or preventive care to reduce workers' comp claims.

Has anyone used cryptocurrency tax software to handle this kind of situation? I tried CoinTracker but it doesn't seem to have a way to properly categorize theft or hacks.

This is a complex situation, but you're on the right track thinking about it as a capital loss. Here's what I'd recommend based on similar cases I've seen: 1. Report the forced Dogecoin sale on Form 8949 with your $26,000 cost basis and $6,200 proceeds - this gives you a $19,800 capital loss. 2. For the Ethereum that was immediately stolen, you technically owned it briefly. I'd treat this as a purchase at $6,200 and then a disposal with $0 proceeds (theft), creating another $6,200 loss. 3. Document everything thoroughly - keep records of the hack, any exchange communications, police reports, and blockchain transaction IDs showing the unauthorized transfers. 4. Consider attaching a brief statement to your return explaining the circumstances. This shows good faith if the IRS ever questions the large loss. The total loss would be substantial, so make sure you understand the capital loss limitations ($3,000 per year against ordinary income, with the rest carrying forward). You might want to consult a tax professional who deals with crypto to review everything before filing. Also, definitely file that police report if you haven't already - it's important documentation for the theft claim.