Does filing an extension because of a late K-1 increase your chances of being audited? I've always heard you should avoid extensions if possible.

Filing an extension does not increase your audit risk at all. That's a common myth. In fact, tax professionals file extensions for many of their clients as standard practice. The key is making sure you pay any estimated tax due when you file the extension. Penalties are for not paying on time, not for filing the actual return later. As long as you make a good faith estimate of what you owe and pay that amount with your extension request, you're completely fine.

This is great advice! I had the same issue with a wrong EIN and it was a nightmare to fix. I'd also recommend comparing the K-1 you receive with any estimated K-1 info your brother might have given you during the year. If there are big differences, ask why before filing.

That's really good to know about the account freezes! Do you know if other payment platforms like Venmo or Cash App have similar issues? Or would you recommend something completely different?

Venmo is actually owned by PayPal so they have similar policies. Cash App can be more flexible but still has its limitations. Many content creators use platforms specifically designed for their industry that have built-in payment processing - these tend to be much more stable since they're designed for that purpose. Some also use multiple payment methods to diversify risk. Another option is to set up a proper business entity (like an LLC) and get a business bank account. This provides an additional layer of separation between your personal finances and business activities, and gives you more professional payment options. It costs a bit to set up but provides much better protection and legitimacy.

Is there a minimum amount you need to earn before worrying about quarterly payments? I do some freelance work but it's pretty irregular and not a ton of money.

Do these mail forwarding services actually hold up if you get audited? I'm worried about setting something up that looks fishy to tax authorities.

Mail forwarding services are completely legal and legitimate for business addresses when properly used. The key is transparency and accuracy in your tax filings. You need to be truthful about where business activities actually occur, regardless of your official address. If you're audited, what matters is where you're conducting business operations, not just where your mail goes. If you claim Wyoming for tax purposes but are clearly operating from Connecticut, that would be problematic. However, many digital businesses can legitimately operate from anywhere. Document your work locations, keep records of travel, and consult with a tax professional to ensure you're handling multi-state issues correctly.

Thank you for sharing your experience! Great point about investors potentially seeing through tax avoidance strategies. Did you end up having to register as a foreign entity in multiple states despite having your Wyoming address? Were there any complications with banking or receiving payments with this setup?

Yes, I did end up registering as a foreign entity in California because I spent significant time working there (over 183 days). The Wyoming address wasn't an issue for banking - I used Mercury for business banking and everything was set up online. They just required my EIN, formation documents, and operating agreement. For payments, no complications at all. Most payment processors and platforms don't care about your physical address as long as you have proper business documentation. The biggest challenge was actually keeping track of where I was working throughout the year for tax purposes. I created a simple spreadsheet to log my location each week, which helped tremendously when tax season came around.

I did a reverse exchange last year. It's definitely more complex and expensive. You need an Exchange Accommodation Titleholder (EAT) to hold the new property while you sell the old one. My qualified intermediary charged about $7K more for this vs a standard exchange. You still have 180 days total to complete everything, but now you're racing to sell your property. If you can't sell in time, you lose the exchange benefits.

Thanks for sharing your experience. That $7K additional fee is steep but might be worth it for this property. Do the same identification rules apply in reverse? Or since I'm buying first, is that part simpler?

Yes, it includes weekends and holidays! The only exception is if the 45th day falls on a weekend or legal holiday, then you get until the next business day. But otherwise, it's 45 calendar days, no extensions. Mark your calendar carefully!

3 Can you explain the pro-rata rule a bit more? I have some old 401k money that I rolled into a Traditional IRA years ago, plus some non-deductible contributions like OP. Will that mess up the backdoor Roth strategy?

22 The pro-rata rule means the IRS looks at all your Traditional IRA accounts combined when you do a conversion. If you have a mix of pre-tax and after-tax money, you can't just convert the after-tax portion. For example, if you have $50,000 in pre-tax Traditional IRA money from an old 401k rollover, and you add $6,000 in non-deductible contributions (after-tax), your IRAs are now about 89% pre-tax and 11% after-tax. If you try to convert $6,000 to Roth, about 89% of that conversion ($5,340) would be taxable. One workaround some people use is to roll pre-tax IRA funds into a current employer's 401k if possible, which removes them from the pro-rata calculation. Then they can do clean backdoor Roth conversions with just the non-deductible contributions.

18 The main downside is that any earnings on that money will be taxed as ordinary income when you withdraw in retirement, rather than being tax-free like they would in a Roth. If you're young and this money will be invested for decades, that's potentially giving up a lot of tax-free growth. Also, tracking basis gets more complex over time if you have a mix of deductible and non-deductible contributions. You'll need to file Form 8606 every year you make non-deductible contributions and keep records potentially for decades.