Thanks for this insight. Our pediatrician has actually written respite care into my daughter's care plan, but nothing specifically about who provides it. Would it help if we got the doctor to write a letter specifically mentioning that having a trusted family member like grandma is beneficial for our daughter's condition since she struggles with new people due to her autism?

Yes, that would definitely strengthen your case considerably. Having your pediatrician specifically document that a familiar caregiver like your daughter's grandmother is medically beneficial due to her autism-related difficulties with new people would create a direct medical necessity connection. The letter should explain why this specific arrangement (flying in grandmother) is medically necessary rather than just convenient or preferable. Make sure the letter mentions your daughter's diagnosis, why consistent caregivers are important for her condition specifically, and how this respite care benefits her medical condition beyond just giving you a break.

I used TaxSlayer last year for a similar situation with my son's therapy travel expenses. TurboTax was too limiting for our complex medical situation. TaxSlayer has a specific section for unusual medical expenses where you can add detailed notes explaining the medical necessity.

2 Wait, Section 179 works for software too? I thought it was just for physical equipment like computers and machinery. Does the software have to be installed on your computer or can it be cloud-based subscription stuff too?

11 Yes, Section 179 absolutely applies to software! Off-the-shelf computer software that's available to the general public, used in your business, and has a useful life of more than one year qualifies for Section 179 deduction. Both installed software and cloud-based subscription software can potentially qualify, but there are some differences. Installed software you purchase outright typically qualifies for immediate Section 179 expensing. For cloud-based subscription services, it depends on the specifics - sometimes these are simply treated as regular business expenses rather than Section 179 property. The key is whether you have rights to the software beyond just accessing it online (like downloading components or having perpetual access rights).

16 Good point! In California, I discovered they have completely different rules about business education expenses. Had to file an adjustment because I assumed the state would follow the same federal guidelines. Cost me an extra $200 in state taxes I wasn't expecting.

That's really helpful, thanks for the warning! Was the amendment process difficult? I'm wondering if I can just do it myself or if I really need professional help with this.

The amendment itself wasn't too complicated. I used the same tax software I originally filed with (TaxAct), and they had a guided amendment process. The trickiest part was figuring out which forms needed to be amended - in my case it was Schedule D and Form 8949 for the investment changes, plus the 1040-X to summarize everything. If your tax situation is otherwise straightforward, you could probably handle it yourself. But given the size of your adjustment (going from a loss to a $37k gain), it might be worth at least consulting with a tax pro. That kind of change could impact other parts of your return like the Net Investment Income Tax or your overall tax bracket.

This! I learned this lesson the hard way. Now I wait until at least March 15th to file if I have any investment accounts. The extra wait for my refund is worth not having to amend.

Thanks for this! My RSUs also vest unevenly - way more in the second half of the year. Where exactly do I find this annualized income installment method option? Is it somewhere in the Form 2210 section?

In both TaxAct and FreeTaxUSA, you'll need to go to the Form 2210 section. It's usually under "Other Taxes" or sometimes "Payments and Penalties." Look for something like "Underpayment of Estimated Tax" or directly for Form 2210. Once you're there, there should be a question asking if you want to use the regular method or the annualized income installment method. Select the annualized option. You might need to check a box that says something like "My income varied during the year" or "I want to use the annualized income installment method." The software will then ask for quarterly breakdowns of your income and withholding, which better accounts for the uneven RSU vesting schedule.

You don't need to attach pay stubs to your tax return. The Form 2210 just needs you to break down your income and withholding by quarters (or months if using the annualized method). If your tax software requires manual input, you'll need to go through your pay stubs and RSU statements to determine how much income you received and how much tax was withheld in each period. The dates on your RSU vesting statements will tell you which quarter to assign that income to.

Did you have any issues when filing your taxes the following year when the incorrect 1099 showed up? I'm worried the IRS computers will automatically flag a mismatch if the client reports it wrong next year.

I did have a small issue the following year - I received a letter from the IRS asking about "unreported income" because the amounts didn't match. I responded with a letter explaining the situation and included my proof (bank statements showing the deposit date in the previous year, copies of invoices, and screenshots of the payment confirmations). I also included documentation showing I had already reported and paid taxes on that income in the correct previous tax year. The IRS accepted my explanation and documentation, and the matter was resolved without penalties. That's why keeping detailed records is so important in these situations.

This is an excellent point! The client might not realize they're setting themselves up for potential issues. The IRS can penalize businesses for failing to file required information returns or filing incorrect ones.