LCBO weirded me out at first too, but there's more beer stores now and then I also spent a lot of time getting my beers direct from the breweries. The breweries are one of the things I am most excited about to be honest!
Affordability obviously means something different to everyone, but having lived in Toronto, London and Dublin the last 5 years and now going back to Toronto, it is far more affordable. This is partly because my salary is higher in Toronto! Condos are cheap right now if you want glass and views but are not exactly bike friendly!
Roncesvalles, beaches, high park/junction - all on our list too. To be honest my priorities are: not too far from Don Valley trails (so max 8km), close to a decent brewery and with space to work on the bikes!