How difficult was it to set up the TOD? Does it offer any advantages over just naming them as regular beneficiaries? I'm trying to keep things as simple as possible while still maximizing the tax benefits.

Setting up the TOD was extremely simple - just a form from my brokerage firm that took maybe 10 minutes to complete. The main advantage is that it's specifically designed for investment accounts and creates a cleaner transfer process. The TOD designation accomplishes essentially the same thing as a regular beneficiary designation, but it can sometimes process more quickly after death and avoids probate. Both methods will give your grandkids the full step up basis benefit. One thing to note - if you have multiple grandchildren and want to specify different percentages or specific assets going to specific grandchildren, the TOD forms typically allow for that level of detail.

Yeah, the UTMA/UGMA accounts are terrible for tax efficiency compared to getting the step up basis. My brother went that route and regretted it. Did you consider a trust at all? I've heard revocable living trusts can provide the step up basis while also giving you more control over when/how the kids get the money.

What about protein powders and supplements that I feature in my workout videos? I often show what I'm using and how I prepare it before workouts. Would those count as "exclusively for content"?

Supplements shown in videos have a stronger case for deductibility since they're being used directly in your content creation. Make sure to document which supplements were used specifically for which videos or content pieces. Save the receipts and note the business purpose (e.g., "Protein powder for supplement review video posted 3/15"). Keep in mind that any portion used outside of content creation would still be considered personal usage. If you buy a container of protein powder, use some in a video, then consume the rest personally, only the portion used directly in content would potentially be deductible. Some influencers track this by percentage or even have separate supplies for business vs. personal use to make documentation cleaner.

My cousin is a CPA and says food deductions are one of the biggest audit triggers for self-employed people. The IRS is especially picky about food because everyone needs to eat, so they scrutinize when people try to deduct it as business. Apparently they've been cracking down on fitness influencers specifically lately.

Thanks for mentioning this! I just checked with my HR department and they confirmed our plan (also Fidelity) does accept IRA rollovers, but only of the pretax portion. They said they'll need a statement from my IRA custodian that clearly shows the breakdown of pretax vs. after-tax amounts. That's really helpful to know before I start the process. One question though - do you know if there's a specific form that Fidelity requires for this? My HR person wasn't sure about the exact paperwork.

For Fidelity specifically, they have a form called "Transfer/Rollover/Exchange Form" that you need to fill out. You can find it on their website or they can send it to you. Make sure you check the box that indicates it's a direct rollover from an IRA to your employer plan. Additionally, you'll need a statement or letter from your current IRA custodian that clearly breaks down the pretax and after-tax portions. Some custodians have a specific form for this, others will just generate a letter if you explain what you need.

This is super important! A buddy of mine got hit with an unexpected tax bill because he did these steps in the wrong order. The timing really matters.

Did you have to do anything special with your bank to make the Direct Pay work? My US credit card always gets flagged for fraud when I try to use it from overseas for anything government-related.

I did have to call my bank first to put a travel notice on my card and specifically mention I would be making a payment to the IRS. Even with that, my first attempt was declined and I had to verify it wasn't fraud via text message. I recommend trying the payment a few days before you need to submit it, just in case you run into issues. My backup plan was to have my parents make the payment from their account in the US if my card kept getting declined. The IRS doesn't actually require the payment to come from your personal account - it just needs to be properly attributed to your tax ID/SSN.

You're not alone in the confusion! Form 2350 is specifically for US citizens or residents who are abroad and need more time to meet either the bona fide residence test or the physical presence test to qualify for special tax treatments like the Foreign Earned Income Exclusion. Form 4868 only gives you until October 15, while Form 2350 can potentially give you more time (up to a 6-month extension, and sometimes more if needed specifically to meet those residency/presence tests). If you're trying to qualify for those expat benefits, 2350 is usually better.

That's a really helpful distinction. Do you think it's reasonable to expect both services from the same person? Or should I be looking for two separate professionals - one for planning and one for preparation?

Most comprehensive CPAs should be able to provide both services, but you may need to specifically request and possibly pay extra for the planning component. Many tax professionals offer tiered service packages - basic preparation at one price point and more comprehensive planning at a higher price. For someone in your situation with increasing income, business activities, and life changes like marriage, I'd definitely recommend finding one person who can handle both aspects. Just be clear about your expectations upfront and make sure they explicitly offer tax planning as part of their services.

Tax software is fine for simple situations but it misses a lot for complex cases. I tried this approach with my small business and rental properties and ended up getting audited because the software didn't properly handle some depreciation calculations. A good CPA is worth every penny for complicated tax situations.

You're right that it's not for everyone. I should have mentioned my situation is pretty straightforward - W2 income, mortgage, some investments. For folks with businesses, rental properties or more complex situations, a CPA probably makes more sense. I still think tax software has gotten much better at prompting for common deductions and credits though. Mine specifically asked about HDHP coverage and whether it was individual or family, then calculated the maximum HSA contribution automatically.