I would start taking a look more on the east side of downtown. think sherbourne, bloor, the lake, DVP
What I'm seeing happening is a type of blender effect.
10 years ago, or even 5 years ago, the east side was really hit and miss for good areas. you had cabbagetown, the distillery, and really nothing else.
now you have so many good spots being developed and maturing on the east side that they are starting to all blend into each other, hence, the blender effect. when you put a bunch of good pockets together it creates something where the sum is greater than all the individual parts.
you can now walk from bloor all the way to the lake and see so much change and momentum happening on the east side all around you.
As you walk south, you have cabbagetown which has always been a nice area,
regent park which is rapidly becoming a great area,
corktown which is finally coming of age,
the west don lands which is going to be a hot spot in just 1 year when the pan am games hit,
the distillery district i believe is still an off-the-radar gem that most people have not yet discovered,
and the east bay front is going to be something special over the next decade.
and honourable mention goes to Riverside, just across the river from corktown/west don lands which is the new home of all east side hipsters and soon they will have their own version of the Drake/Gladstone hotel with
@Streetcar Developments purchase of Jilly's.