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The people at H&R Block have for the second straight year offered a list of odd questions fielded by their tax preparers. This year’s batch is both fun and informative:

Q: I haven’t filed my taxes in 3 years. If I file them all together, am I going to raise suspicions and be put on some sort of criminal watch list?

A: While it is illegal in Canada to fail to file a tax return, no, you will not be flagged or put on any criminal watch list.

Q: I bring my dog to work every day. Although he isn’t a registered service animal, are there any tax benefits I can claim for him as he provides emotional support to our entire office?

A: You are not able to claim your dog in this instance. Expenses are only eligible if they are in respect of an animal that has been specifically trained to perform tasks that assist a patient with a severe mental impairment. Examples of tasks psychiatric service dogs could perform include: guiding a disoriented patient, searching the home of a patient with severe anxiety before they enter and applying compression to a patient experiencing night terrors.

Q: My job requires me to wear a nice suit, and I've been flagged for my suit looking a little on the cheaper side. Since this is a requirement of my job, can I claim it as a business expense?

A: Generally speaking, clothing isn’t normally considered a business expense, so a designer suit picked up for an office job can’t be claimed. However, you may be eligible to claim your business attire on your taxes if there is absolutely no chance you would wear those clothes on your own time. However, in order to make these claims you will need a signed Declaration of Conditions of Employment (T2200) indicating you are required to pay these expenses.

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Rob’s personal finance reading list…

A new tip on tipping in restaurants

I know from experience that readers of this newsletter have strong views on tipping. Here’s an article from a U.S. website that explains a “tipping trick” that can save you over US$400 a year. Check out this thread on Twitter for the savagely critical response. And here’s something on tipping housekeeping staff at a hotel.

Saddest personal finance story of the year

Young adults in the United States are selling part of their future earning power after graduation to finance their education and avoid student debt. Through what’s called an income-sharing agreement, investors agree to fund a student’s education in exchange for a share of earnings for a period of time after graduation.

A meal plan that saves time, money and sanity

A financial planner presents a three-week meal plan for busy families. Simplifies grocery shopping and meal prep. A template for starting your own plan is included.

Cheap and easy ways to boost the value of your home

A black front door is on the list, and so is moving to a home near a Starbucks.

Today’s financial tool

Last-minute tax filing tips from the Canada Revenue Agency, including a link to free online tax software you can use to file electronically.

Tell Rob

There’s a great point about car loans in this response to a comment I made in a recent newsletter about limiting car loans to five years and $400 per month, max.

Open this photo in gallery:

Steve Bridge, CFP/Twitter

Do you have a question for me? Send it my way. Sorry I can’t answer every one personally. Questions and answers are edited for length and clarity.

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