Don't forget you need to answer the crypto question on Form 1040! Even if you just HELD crypto and didn't sell any, you need to check "Yes" to the question asking if you had any transactions involving digital assets. The IRS added this a few years ago and they're using it to track who has crypto.

Thanks everyone for all this detailed info! @Ellie Kim - you're definitely not alone in feeling overwhelmed by crypto taxes. I went through the same thing last year and it's way more manageable once you break it down. A few additional tips that helped me: - Keep detailed records throughout the year, don't wait until tax time. I use a simple spreadsheet to track each transaction as it happens. - If you're using multiple exchanges, download ALL your transaction histories as CSV files before you start. Some exchanges only keep records for a limited time. - Don't forget about any crypto you might have earned through things like Coinbase Learn rewards, airdrops, or referral bonuses - those count as income at fair market value when received. The specialized crypto tax software really is worth it if you have more than just a few simple buy/sell transactions. I tried doing it manually my first year and made so many errors I had to file an amended return. The peace of mind alone makes the software cost worthwhile. Good luck with your filing!

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.

This is exactly the kind of question I had when I was considering the same move! Based on my experience and research, I can confirm what others have said - your qualified dividends will absolutely maintain their preferential tax treatment even when held through a single-member LLC. The key thing to understand is that the IRS treats a SMLLC as completely transparent for tax purposes. It's like the LLC doesn't exist from a tax perspective - all the income, including qualified dividends, flows through to your personal return with the same character it would have if you owned the investments directly. One practical tip: when you do make the transfer, work with your broker to ensure it's done as a non-taxable transfer rather than a sale and repurchase. Most brokers can handle this as an "in-kind" transfer to avoid triggering any capital gains. Also, while the tax treatment stays the same, don't underestimate the administrative overhead. You'll need that EIN, separate bank account, and good record-keeping practices. But for $8,500 in annual dividends and the asset protection benefits you're seeking, it's probably worth the extra paperwork. Just make sure you have adequate liability insurance too - the LLC isn't a magic bullet for all risks!

Has anyone tried using the IRS's own free file fillable forms to claim the Lifetime Learning Credit? I'm thinking about doing that instead of paying TurboTax.

I totally feel your pain with TurboTax's sneaky upgrade tactics! I went through the exact same thing last year and it's so frustrating when you're already trying to save money as a student. Here's what worked for me: I ended up switching to FreeTaxUSA which includes the Lifetime Learning Credit in their free federal filing. The interface isn't as polished as TurboTax but it gets the job done and saved me that $49 upgrade fee. They do charge like $15 for state filing, but that's still way less than TurboTax's upgrade. If you want to stick with completely free options, definitely check out the IRS Free File program like Taylor mentioned. Just make sure to go through IRS.gov directly - don't Google the tax companies because they'll redirect you to their paid versions instead of the actual free file versions. One tip: before you abandon your TurboTax progress, take screenshots of all your entered information or print the review pages. That way if you switch services, you'll have all your data organized and won't feel like you're starting from scratch. The Lifetime Learning Credit is worth up to $2,000, so it's definitely worth the effort to avoid paying TurboTax's upgrade fee!

Pro tip: If you're having trouble reaching the IRS, try contacting your local Taxpayer Advocate Service. They can sometimes help push things through faster.

Just want to add another option that worked for me - you can also try updating your direct deposit info through the "Where's My Refund" tool on the IRS website. It's not always available depending on where your return is in processing, but if the option shows up, it's way easier than calling. I was able to change mine online without having to deal with phone wait times at all. Worth checking before you spend hours on hold!

Just a warning - my parents set up an irrevocable trust in 2014 and we've had nothing but headaches. The tax filing requirements are a NIGHTMARE. We have to file a separate trust tax return (Form 1041) every year which costs about $900 with our accountant. Plus the trustee fees are eating into the assets. And now my mom needs some of the money for a special medical treatment but we can't access it because, surprise, it's irrevocable! Our attorney didn't emphasize enough how permanent this decision would be. Consider a revocable trust that converts to irrevocable upon death instead. Much more flexibility during lifetime.

This is such a timely question for me! I'm in a similar situation with my aging parents and have been wrestling with the same decisions. One thing I learned from my estate planning attorney is that the key advantage of an irrevocable trust isn't just the estate tax savings - it's also the "valuation discount" you can get. If your parents are transferring business interests or real estate (like that vacation property), they might be able to claim a discount on the value for gift tax purposes since the beneficiaries won't have immediate control. For your situation with $650K in total assets, you're definitely in the range where an irrevocable trust could make sense, especially with the vacation property appreciation potential. But I'd strongly recommend getting a second opinion from an estate planning attorney who specializes in irrevocable trusts before making the decision. The flexibility concern is real - once it's done, it's done. Some attorneys can build in limited flexibility through trust protectors or distribution standards, but you need to plan for worst-case scenarios upfront. Have you considered what happens if your parents need long-term care or have other major expenses?