Thanks for this suggestion! I've been digging through their paperwork and found they actually have very few statements from the last 5 years. I'm wondering if these notices went to an old address or something. Would the insurance company have records of what notices they sent and when? And if they didn't properly notify, what's the best way to approach them about it?

Insurance companies absolutely keep records of all notices sent, especially important ones like impending lapse notifications. Request a complete communication history from the company - they're required to maintain these records. If you find they didn't properly notify your parents according to state regulations, start with a formal written complaint to the company referencing the specific notification requirements they failed to meet. Include a clear request to reverse the lapse and reinstate the policy. If they don't respond appropriately, file a complaint with your state's insurance commissioner or department of insurance. These regulatory agencies take notification failures seriously, especially with older policyholders.

My father-in-law managed to get his partially reversed. The key was finding documentation showing the insurance company had been sending notices to an outdated address despite having his current contact info on file for other communications. He filed a complaint with the state insurance commissioner and eventually got about 60% of the taxable amount waived. The company reinstated his policy with reduced benefits rather than treating it as fully lapsed.

Wouldn't using an LLC mean losing the mortgage interest deduction? I thought you could only deduct mortgage interest on your primary residence if you personally own it, not if it's owned by an LLC?

You're right to question this - an LLC typically would cause you to lose the mortgage interest deduction for a personal residence. What we actually did was create a partnership agreement rather than a full LLC (I simplified in my original comment). The partnership agreement gives us similar protections in terms of clearly defining ownership and responsibilities, but allows the property to remain in our personal names for tax purposes. This way we each get to deduct our portion of the mortgage interest while having clear documentation of our arrangement. Tax rules around entity structures can get complicated, so definitely consult with a tax professional before going this route.

I don't think that's correct. The annual gift tax exclusion is $17,000 per person for 2023 (probably higher for 2025), and it's only an issue if you exceed that amount. Plus, you'd have to file a gift tax return but probably wouldn't owe any actual tax unless you've used up your lifetime exemption, which is over $12 million.

Thanks for this clear advice! So for our email blast, we should focus on the donor's local time rather than our organization's time zone. That makes it much easier to communicate. Do you have any suggestions for how to handle international donations where the donor might be in a completely different calendar day? We have supporters in Asia and Australia who sometimes make year-end gifts.

For your international donors, I'd recommend adding a specific section in your email addressing them directly. Something like: "For our international supporters, please note that donations are recorded based on the date and time in YOUR location. If it's December 31st where you are when you complete your donation, it will count for this tax year." For donors in countries with different tax systems, you might want to add that this guidance is specific to US tax law, and they should consult their local tax regulations regarding charitable contributions if they're claiming deductions in their home country.

Unfortunately, you can't alter the official timestamp on donations that have already been processed - that would raise red flags with the IRS. However, if you had a documented system outage, you might be able to provide donors with a statement explaining the technical issue. In some cases, donors might be able to claim the deduction based on when they initiated the transaction rather than when it completed, but they would need solid documentation. For future years, I'd recommend implementing a contingency plan for your system during high-volume periods like year-end, and possibly closing online donations a few hours before midnight to avoid these issues.

Thanks for the advice! Do you recommend any specific accounting software that's not too complicated for beginners? Also, can I just open a regular personal checking account for this or do I need a formal "business" account?

For beginners, I'd recommend something simple like Wave (it's free) or QuickBooks Self-Employed if you want something more robust but still user-friendly. Both let you track income and expenses, and can generate reports you'll need for taxes. For the bank account, a regular personal checking account works fine when you're starting out, but open one that's ONLY used for your business transactions. This makes tracking much easier and creates a clear separation that's helpful if you ever get audited. As you grow, you might want to upgrade to a proper business account for more features, but that's not necessary right away.

This is so confusing... how do you even figure out which states you need to pay tax to if you're selling online to people all over?

Thanks for mentioning this! I would have totally messed that up. Do you know if I need to include all the original attachments again or just the ones I'm changing?

You only need to include the forms and schedules that you're changing with your Form 1040X. So definitely the Schedule C for your business expenses, but if you're not changing other aspects of your return, you don't need to include those other forms again. Also, you'll need to file a separate 1040X for each tax year you're amending. Don't try to combine multiple years on one form - the IRS will reject it.

Good advice. Also worth noting that the IRS generally has 10 years from the date of assessment to collect taxes owed. So depending on exactly when these returns were filed/assessed, the collection statute of limitations might be approaching.