Is there a way to do a quick check for these hidden characters across my whole return? I'm using TaxAct and now I'm worried there might be backslashes I'm not seeing.

The best way to check your entire return is to create the PDF preview (usually there's a "Preview" or "Print Preview" option) and then use the search function (Ctrl+F on Windows or Command+F on Mac) to search for the backslash character. Just type \ in the search box and it will highlight any instances throughout the document. TaxAct also has a built-in error checker that runs before you file. While it might not specifically call out backslashes, it should catch most formatting issues that would cause rejection. If you're still concerned, you can also print the entire return and visually scan the fields where you entered text (like name, address, occupation) for any unexpected characters.

Forward slashes can definitely cause similar problems. The IRS systems interpret them as date separators or division operators in some contexts. I'd recommend removing them from any text fields like addresses. Only use them where they're expected (like in dates formatted as MM/DD/YYYY).

Did FreeTaxUSA handle state taxes too or just federal? And was that included in the basic price or an add-on?

FreeTaxUSA does federal returns for free and charges around $15 for state returns, which is way cheaper than most other services. The state filing is an add-on but still very affordable compared to the $40+ that TurboTax and others charge. They handle both federal and state unemployment reporting correctly, which was important for me since my state taxes unemployment a bit differently than federal.

I tried their app last year and honestly wouldn't recommend it. Super buggy and kept crashing when I tried to upload photos of my documents. Ended up having to use the website anyway. If you're set on using your phone, TaxSlayer's app worked better for me this year.

How did you handle insurance and liability issues with renting out heavy equipment? I'd be terrified someone would hurt themselves and I'd get sued into oblivion.

I purchased a specific commercial equipment insurance policy that covers rental use. It was about $1,800 annually but well worth the protection. I also created a simple LLC to own the equipment and had renters sign a detailed liability waiver that my attorney drafted. Most equipment sharing platforms also offer some basic insurance coverage as part of their service, though I wouldn't rely solely on that for heavy machinery. The key is being properly insured and having clear documentation of the equipment's condition before and after each rental.

Your accountant is partially correct but missing some nuance. Land itself is never depreciable, and certain permanent improvements to land (like grading or clearing) must be capitalized to the land basis. However, the equipment used to make those improvements is separate from the improvements themselves. If the equipment is used in a business or income-producing activity, it can typically be depreciated regardless of what you're using it for. The key distinction is between the equipment (depreciable asset) and the permanent land improvements (capitalized to land basis).

Thanks for mentioning this! I'm in Illinois. I've actually started keeping a detailed log of my hours and payments since August (wish I had done it from the beginning). Do you know if there are any Illinois-specific requirements I should know about?

Illinois does have some specific requirements for household employers. They need to register with the Illinois Department of Employment Security if they pay $1,000 or more in a calendar quarter. They're required to pay Illinois unemployment insurance taxes. Illinois also has a Domestic Workers' Bill of Rights that provides additional protections for nannies and other household workers. Your employers should be providing you with an employment notice that outlines your wage rate, work schedule, and other employment terms. Since you're paid in cash, make sure you're getting some form of pay stub or record showing hours worked and wages paid.

I used TurboTax last year as a nanny. It worked fine for reporting my income with the W-2 my employer provided, but it doesn't help much with the situation where your employer isn't doing things correctly. If you need to file Form SS-8 or 8919, you might need to do that separately outside the software.

Is a Private Letter Ruling actually worth the cost though? I've heard they take forever to get (like 6-9 months) and by then your investment opportunity might be gone. Have you actually done one yourself for an IRA transaction?

You're absolutely right about the timeframe - they typically take 6-9 months, which makes them impractical for many time-sensitive investments. I haven't personally done one, but a business partner did for a significant real estate investment he was considering through his self-directed IRA. For smaller investments, the cost usually doesn't make sense. But if you're considering a large transaction with millions at stake, or a recurring investment strategy you plan to use multiple times, it can be worth the peace of mind. In my partner's case, the PLR actually saved him from making what would have been deemed a prohibited transaction, potentially saving him hundreds of thousands in taxes and penalties.

A Roth conversion ladder won't help after a prohibited transaction has already occurred. Once the prohibited transaction happens, the IRA is immediately considered distributed as of January 1 of that year. It's no longer an IRA that can be converted to a Roth. You could potentially use the distributed funds to contribute to a new Roth IRA (subject to income limits and annual contribution caps), but you'd still owe taxes and penalties on the full distribution from the disqualified IRA first.