Was the process of uploading documents easy? And did they contact you with questions or just handle everything behind the scenes? Thanks for sharing your experience!

The document upload process was pretty straightforward - they have a secure portal where you can drag and drop files or take pictures with your phone. They categorize everything for you. My tax pro did contact me twice with questions. Once about some business expenses that needed clarification and another time about my home office deduction. The communication was all through their messaging system in the portal. After I answered those questions, they completed everything within about 3 days. Then they sent a draft for me to review before filing. I appreciated that they didn't just make assumptions and actually took the time to verify things they were unsure about.

I've used both. TurboTax Live Full Service was slightly more expensive ($229 vs $199 for H&R Block) but I found their interface more user-friendly. The tax pros seemed about the same level of expertise at both places. Main difference was TurboTax had more available time slots for video reviews where you could actually see/talk to your preparer.

What's the difference between a tax preparer and a CPA? Would a regular tax preparer be able to handle real estate investments from another country or is that something only a CPA should handle?

A CPA has more extensive education, passed the CPA exam, and maintains specific continuing education requirements. Tax preparers like me have various levels of certification (I'm an Enrolled Agent which means I'm licensed by the IRS). For international real estate investments, I would strongly recommend a CPA with specific experience in that area. While some experienced EAs could handle it, CPAs typically have more training with complex international tax issues. Foreign real estate can involve foreign tax credits, FBAR filings, and other complex reporting requirements that go beyond basic tax preparation. This is definitely a situation where expertise matters more than price.

This depends entirely on the complexity. For simple returns, sure. But for real estate investments, especially with foreign ownership, earlier meetings can be crucial for gathering all the required documentation. Sometimes these returns require information that takes weeks to track down.

Doesn't creating an LLC and doing the S-Corp election cost a lot in administrative fees? I've heard you need to run payroll and everything. Is it really worth it for just one property?

You're right that it doesn't make financial sense for just one property. The administrative costs (state filing fees, payroll service, possibly a CPA) would likely outweigh the tax benefits until you have multiple properties generating significant income. For a single property, increasing your W-4 withholding or making quarterly estimated payments is definitely more cost-effective. I'd say the S-Corp approach usually starts making sense around 3-5 properties or when rental income exceeds about $40,000 annually. Until then, the simpler approaches others have mentioned are your best bet.

This is really important. Depreciation is actually required by the IRS even if you don't claim it. And they'll hit you with depreciation recapture taxes when you sell regardless. So definitely claim it!

Where exactly do you report the Roth vs traditional breakdown? I have both in my solo 401k but can't seem to find where this goes on the 5500-SF. Is it in Part III?

You'll need to complete Part VI of Form 5500-SF if you have both Roth and traditional components. Look specifically at line 11a and 11b where it asks about pre-tax and designated Roth contributions. The total combined value goes on line 7 of Part III, but the breakdown between traditional and Roth gets reported in Part VI. It's easy to miss because most of the solo 401k guidance focuses on the asset reporting and not this specific detail.

I was about 3 months late filing mine last year and did get a notice with a proposed penalty. I called and explained that as a small business owner I wasn't aware of the requirement, and they actually waived the penalty completely. I think first-time abatement is pretty common. Just don't ignore it!

That's a relief to hear! Did you have to submit anything in writing or was the phone call enough to get the penalty waived? I'm about 6 weeks late at this point.

That's really helpful to hear a real-world example! Did you have to do anything special on your tax return to document the rollover and subsequent withdrawal? And did your 401k plan administrator automatically provide that contribution/earnings breakdown, or did you have to specifically request it?

You'll receive a 1099-R from your 401k provider showing the total distribution, and you'll need to report the rollover on your tax return. For the withdrawal, you'll get a 1099-R from your IRA custodian the following year. I didn't need to file any special forms since my withdrawal was less than my total contributions, but I did keep detailed records of my basis. My plan administrator provided the contribution/earnings breakdown automatically as part of the distribution paperwork. If yours doesn't, definitely request it - you need this documentation to establish your basis. Some administrators have this readily available, while others might require you to specifically ask for a "distribution statement showing contribution and earnings portions.

Wait I'm confused. So if I open my first ever Roth IRA today at age 55, then immediately roll over my Roth 401k that I've had for 20 years, I still have to wait until age 60 to access the earnings tax-free even though I'll be past 59.5?

That's exactly right. The 5-year rule for Roth IRA earnings requires that your first Roth IRA was established at least 5 tax years ago AND you're 59½ or meet another exception (disability, first-time home purchase, etc.). So in your example, if you open your first Roth IRA at 55 and roll over your 20-year Roth 401k, you could access all the contribution portions immediately without tax or penalty. However, for the earnings to come out tax-free, you'd need to wait until both: 1) you're 59½ (which you already are), and 2) it's been 5 tax years since you established your first Roth IRA - so that would be at age 60.