I like the doubles and polourie at the Midland/Lawrence shop but yeah Drupaties have it in spades for a nice roti.
WC, Cabbage town is not the place for Caribbean food. In fact I do not recall any Caribbean shops there at all. It was a very artsy/beatnik/hippy/yuppy/old Toronto type of neighbourhood. It went through some unfortunate changes over the last few years. Still some nice houses off the main streets - but you're paying for house not yard. The yards are about 3 inches by 4 inches. The apartments at Wellesley were nice once upon a time. I almost rented the top floor of a house around there. But when I realized I'd be a single female in a house full of male students and had to share a bathroom with one. It was real sweet though but I decided not to be a 'tigress'.
There was a nice South American club called Tappas further down at Gerard but that vanished a million years ago.
The area is the setting for Nalo Hopkinson's "Brown Girl in a Ring" (one helluva book, I recommend it!).
Dunno why you're asking but to live? Not I. But I'd stroll thorugh once in a while.
If I had my d'ruthers and was looking to live in Toronto again. My choice would be the Avenue Road and Eglinton area - just south of Eglinton. I'm a bit of the artsy type and love those town homes and condos. I'm not a gardener so a roof top lil garden works for me. It is not very diverse - mostly Jewish, old money - close to Upper Canada College and some of Toronto's oldest churches over on Yonge. Can get a bit tight during rush hour. Expensive but then Toronto is a very expensive city to live in.