In general, I'd say montreal is TG friendly
except maybe if you go in some more seedy
(but still not that bad) peripheral distict.
Montreal is very safe to walk alone at night in.
Bizarely, one of the most accepting areas
in the most dangerous ones, not just for TG
but for everyone: the Gay quarter, just east of
UQAM's latin quarter overlaps a drug dealing
district downtown. But, that's by Montreal
standards, but US standards, this area
is as safe as the safest US ones :-).
Anyway, if you stay away from
the dealers in backstreets, you're very safe.