I think it's cute that you're planning to have a baby and large dinner parties at the same time in a 2 bedroom condo. Maybe my experience with little kids was unique (I doubt it) but I was way too tired to throw dinner parties. A condo (where a sleeping kid is very close to the party) makes that more like a sitcom scenario than a lifestyle, imo.
Sounds like selling your 1 br for $500K+ and buying something like this would be perfect:
https://www.realtor.ca/real-estate/2...gary-sunnyside
An extra 1000 square feet, still a very walkable neighbourhood (kensington shops, downtown, etc)