Hey Spencer! Sounds like you are going to live in while you reno and suite out the basement? Similar to what I'm doing now. Braeside is a good spot. Pretty good transit access, nice mature neighborhood and good lot sizes. My neighborhood is similar in age (Silver Springs), I'm currently completing my basement suite as well while I live upstairs. From that perspective of buying a SFH and converting it to 2-units, I think the numbers can work. It's tougher without that value-add though. I'd be happy to chat more about my experiences if you'd like.
For now I've got this one in Calgary and plan to repeat once more as I've learned a bunch in the process. Later this year I'd like to add one more property - have not decided on where quite yet.
For your project, I'd really recommend going the legal route with the city, rezoning if required, and meeting the additional code requirements of a legal suite as tough as some of them are. I believe that's the best way to get the value and equity out afterward.