Thanks for this perspective! What's the typical price difference between H&R Block vs an enrolled agent? And what specific questions should I ask to make sure they're familiar with server income/tip reporting?

H&R Block typically charges $200-300 for your situation, while independent enrolled agents often start around $150-250 for similar complexity. The key difference is personalized attention and expertise. When interviewing a tax professional, ask them: "What specific documentation do you need for properly reporting cash tips versus reported tips?" A knowledgeable preparer will mention Form 4137 for unreported tips and explain how tips affect your Social Security earnings. Also ask: "How do you handle capital gains when the broker hasn't provided complete basis information?" They should discuss Form 8949 and methods for documenting your original purchase price.

YES! Same thing happened to me. I was using a different tax place (not H&R) but when I switched to doing it myself, I realized they never asked about my TIPS training certification costs or my server book purchases. All deductible! I also file HOH with a dependent and found the child tax credit stuff pretty straightforward.

Exactly! I think a lot of these mass-market tax places just rush through everything too fast. I spent maybe an hour more doing it myself but found like $300 more in deductions. Plus I learned a lot about what I can claim next year. The stock stuff was a little tricky but the software walked me through it.

Wait, can you explain more about the QBI deduction? I thought that didn't apply to rental properties unless you're classified as a real estate professional? I'm just doing this on the side while working a full-time job.

You're right that the full benefits come when you qualify as a real estate professional, but there's still potential QBI benefit for "side" landlords. Revenue Procedure 2019-38 created a safe harbor that allows certain rental real estate enterprises to be treated as businesses for the QBI deduction. To qualify, you need to keep separate books and records for the rental activity, perform 250+ hours of "rental services" annually (less than the 750 for full pro status), and maintain contemporaneous records of your time spent. Even if you don't meet the safe harbor, you might still qualify under the general rules if your rental activity rises to the level of a "trade or business" rather than just an investment.

The Self-Directed IRA for rentals works but has serious limitations. You can't do ANY work on the property yourself - not even changing a lightbulb. You must hire a property manager and third parties for everything. Also, you can't use any personal funds to pay property expenses - everything must come from the IRA itself. The bigger issue is that you lose all the normal tax benefits of direct ownership - no depreciation deductions, no mortgage interest deductions, etc. Plus, if you use debt financing (mortgage), you'll trigger UBIT (Unrelated Business Income Tax) on the portion of income attributable to the debt.

How much is the fee to set up a payment plan online? Is it better to just pay in full if you can?

The fee for setting up an online payment plan is currently $31 if you do direct debit payments. It jumps to $130 if you pay by check or money order. So yeah, if you can pay in full, that's always best to avoid fees and interest. Always better to pay in full if possible since the IRS charges both setup fees AND ongoing interest for payment plans. The interest compounds daily too, which adds up fast.

Yes, if you still have an outstanding tax debt when you file next year and are due a refund, the IRS will automatically apply that refund to your outstanding debt. It's called a tax offset. They'll send you a notice explaining that they applied your refund to previous tax debt.

Thanks for explaining! That's actually not terrible then, kinda like an automatic payment I guess. At least the money's not just disappearing into a black hole lol.

Does Cash App Taxes handle state returns too? Also wondering if they're reliable for more complicated situations like if I have some freelance income next year?

Yes, Cash App Taxes includes state returns for free as well. They can handle freelance income with Schedule C, but they do have some limitations. They don't support multiple state filings, foreign income, or more complex situations like farm income or at-home business depreciation. For most people with W-2 income, some investments, and side gig/freelance work, they work perfectly fine. Just make sure to check their list of limitations if you have anything unusual in your tax situation.

While I get your point, this isn't great advice. The 1099-B is reported to the IRS by the broker, so they actually do know about the $5 gain. If there are mismatches between what's reported to them and what you report, it can trigger automated flags in their system. I'm not saying they'll audit over $5, but why risk it when there are legitimate free options to report it correctly?

What about if my side hustle truly can only be done in certain locations? I make custom furniture and sometimes source special wood when visiting my parents in Oregon. These woods aren't available where I live.

That's a more defensible position. If you can document that you're sourcing materials unavailable in your area, and if this activity is central to your business model, you've strengthened your case for the business purpose of the trip. Keep receipts for the materials purchased, document why these specific materials are necessary for your business, and maintain records showing how these purchases translate into business products and revenue. Remember though - if visiting parents is still the primary reason for timing the trip, you might only be able to deduct the specific business activities (like the extra mileage to visit lumber suppliers) rather than the entire trip cost. The IRS will still look at whether you would have made this trip without the personal component.

I went through one last year for my consulting business. What saved me was having a detailed calendar showing all appointments before the trip was booked, emails setting up meetings, receipts with business purpose noted, and a time log showing how many hours were spent on business vs personal activities. The auditor specifically mentioned that having documentation created BEFORE the trip (proving business intent) was key.