That's interesting about the stepped-up basis, but unfortunately the house was solely in my name from the beginning. We never did a joint ownership. However, I did install a wheelchair ramp and some bathroom modifications for him last year. I hadn't even thought about claiming those as medical expenses! Is there a specific form I need to use for that?

Since the property was solely in your name, you're right that the stepped-up basis wouldn't apply. However, those modifications for your father's care are definitely potential medical expense deductions. You would claim these on Schedule A as itemized deductions under medical expenses. You'll need to keep receipts for the wheelchair ramp and bathroom modifications as supporting documentation. Remember that total medical expenses are only deductible to the extent they exceed 7.5% of your adjusted gross income. If the modifications were substantial, they could help you reach that threshold, especially combined with other medical expenses you may have incurred.

I used FreeTaxUSA last year for a similar scenario with my aunt's house. It was actually much clearer than TurboTax for entering the capital gains info. They have a specific section for sale of home where you can indicate it wasn't your primary residence, and then it walks you through calculating your basis and gain or loss. So much cheaper than TurboTax too!

Good point about state taxes! I'm in Illinois and haven't even thought about that side of things. Would I use the same 1040-ES form to calculate what I might owe the state, or is there a separate process for that?

For state taxes, you'll need to use your state's specific forms, not the federal 1040-ES. Each state has its own estimated tax forms and procedures. For Illinois, you'll want to look up form IL-1040-ES, which is their estimated tax payment form. States also have different thresholds and requirements for when you need to make estimated payments. Some states follow the federal safe harbor rules, while others have their own unique requirements. I'd recommend checking the Illinois Department of Revenue website or giving them a call to confirm their specific rules about estimated taxes for self-employment income.

Is the self-employment tax deduction an itemized deduction or can you take it even if you use the standard deduction?

Thanks so much for this! I didn't even think about getting an actual rejection letter from the SSA. I just assumed since he's on a tourist visa that would be obvious, but I guess they need it officially documented. Did you have to make an appointment at the Social Security office or could you do it online?

We had to go to the Social Security office in person with her passport and visa documentation. You can't do it online unfortunately. We made an appointment through the SSA website which saved us from waiting for hours. The appointment was quick - they reviewed her documents, confirmed she wasn't eligible based on her visa type, and gave us a formal letter stating she was ineligible for an SSN and would need to apply for an ITIN through the IRS instead. That letter was exactly what the IRS needed to process the W7.

This is helpful! My girlfriend and I are planning to marry next year and she'll need an ITIN. Did you send your wife's actual passport in the mail? That seems so risky!

How's the reporting feature? I need to be able to generate reports for specific time periods or clients.

The reporting is actually one of its strongest features. You can generate reports by client, project, time period, expense category - pretty much any way you want to slice the data. I run quarterly P&L reports for my own tax planning, but also generate client-specific expense reports when I need to justify certain pass-through costs. They've also added a dashboard feature that gives you a real-time view of outstanding invoices, expenses by category, and profitability by client. I check it weekly to make sure I'm staying on track with my financial goals.

I used Everlance for about 6 months. It's decent for mileage tracking but pretty basic for everything else. The automatic trip detection was hit or miss for me - sometimes it would record random trips when I was just sitting at my desk! The receipt scanning is okay but not great for complex receipts. If your needs are simple and mainly mileage-focused it might work, but I switched to something more comprehensive.

Thanks for the insight! Sounds like it might not be robust enough for what I need. I've got a lot of different expense types beyond just mileage.

1 I actually tried that already but it seems my employer never set up employee access for us. When I called Paycor directly, they told me they can only provide W-2s to the employer, not directly to employees. So frustrating! But thanks for the suggestion.

3 That's really frustrating - sorry to hear it. Paycor definitely has the capability to give employees direct access, but your employer has to enable it. This is why I suggested Form 4852 might be your best option at this point since we're getting close to the filing deadline.

2 Wouldn't filing with the substitute form be easier than dealing with an extension? Seems like extra steps just to avoid using Form 4852. Plus waiting till October just gives this employer more time to be irresponsible imo.