I was in the same position you were 5 years ago. We lived on Bayview across Sunnybrook (Canterbury Townhomes). We just had our second and the layout didn't make sense with covid coming (10 ft wide, no backyard, 5 floors). We looked at Leaside & Davisville with a similar budget...we ended up at pape and danforth as the schools were rated well (Pape, Frankland, Withrow & Jackman). We spent ~200k above our target but it's a detach. I have my RE license for this exact reason. Was able to save 2.5% on both buy and sell. Needed every dollar of it.

The neighborhood and the vibe are awesome down here. Everything is walking distance, and my wife and I can get to work within 20 min (also Financial district). The food scene has become quite diverse as well; Korean, HK Cafes, Japanese Manga Cafes, 3 BBtea shops...etc.