Another head slap moment!

Sometimes things happen, and you're left scratching your head in befuddlement.

First, some background, so you can fully appreciate what I'm about to lay on the table that we can collectively trudge through the quagmire mentally as we sort out the realities of life as a senior citizen in Canada. It helps to know that my mom and dad created an Ontario company decades ago to to legally run my dad's medical practice. While he was the source of the dollars, she managed the office, a responsibility that included dealing with OHIP and their accountant.

I tell you that so that you can fully appreciate that she's a sharp one, ma mere, and no stranger to dealing in finances, satisfying the CRA, and following the prescribed rules.

At a point in their lives when things were rolling along like a well oiled machine, they fell in love with the idea of buying property in Florida, mostly to provide a welcomed escape from our "lovely" Canadian winters, but also as a solid investment of those hard-earned dollars. On the advice of their financial people, factoring in the inevitable selling of the property, they decided to purchase their condo through the company so that any gains from the sale would be taxed at a corporate rate, in addition to avoiding personal capital gains taxes. The ownership years flew by, and while they thoroughly enjoyed their FLA life, my father's retirement meant that the company transitioned from income earning to simply a holding function for its only asset, the condo. Dad's untimely death meant from that point forward, mom was on her own when the sale was going to happen. She faithfully submitted her business tax return each year, a task that I helped her with so that she could accurately fill out the necessary forms and get them printed to be able to submit to the CRA. 

All of that was "smooth sailing" for a long time.

Fast forward to 2024, mom finally made the angst-ridden decision to sell, closed the deal, and filed the necessary payments with both the IRS and FLA for the FIRPTA taxes accompanying the sale of property as a foreign entity. With no previous experience in this realm, my eyes bulged at the volume of cash that was required to be left in the US ... Close to $200 K in US dollars in total between the two! 

Since December 2024, she has hit brick wall after brick wall in attempting to finalize the deal with the IRS, mostly thanks to the Orange Mussolini's dismantling of government agencies through his henchman Musk's hack and carve job of the IRS ... DOGE indeed. Despite our playing by the rules, the IRS can't seem to cross their T's and dot their I's to put the deal to bed, directly delaying mom's ability to fold her company. She taught me that Canada and the USA have a reciprocal agreement where she can avoid paying taxes twice, but she can't prove to the CRA that she's paid the US what was owed so that she doesn't have to pay the CRA. Multiple filings, inquiries, and requests to the IRS has prompted a steady stream of "we have your file but need another 60 days to evaluate" communication.

All of that is frustrating enough on its own.

To make matters worse, my 86 year old mother recently received a letter from the CRA informing her that she owed $1000.00 as a penalty for filing her business tax return via Snail Mail. After the initial shock and awe of the letter, we researched the tax code in an attempt to understand how that could possibly be true. Our dive into Google-dom revealed that in 2023, the CRA enacted ruling 150.01 requiring all Canadian businesses to file electronically, and despite accepting her 2025 filings they way they have for decades ... 2024 was filed by the accountant that was helping her deal with the IRS ... the 2026 filing was not acceptable and she would have to pay a fine for doing so. Of course, there's an incredibly short deadline with the threat to additional interest fines if not paid ASAP.

WTF???

In our efforts to solve this issue, we've talked to a few people, and everyone reflexively reacts exactly the same way we did, anger instantly rising just like ours. While we understand that the CRA is following their own rules, the fact that they have no sympathy for an 86 year old widow is caught in the quagmire of the IRS machine while struggling with a world that increasingly forces seniors to cope with everything being done online, is maddening, frustrating, and irksome to the Nth degree.

Of course we have to agree to pay the fine.
We're thankful that she's in a position to be able to.
Thing is, what kind of rule is this, considering that some seniors that can't file online?

Be better CRA, especially in times like these.