what looks dark and gloomy to you right now will look beautiful come summertime. The inner-city never looks great in the winter. Little Italy is very safe, by the way, most of the city is. Since you seem to be a little picky, maybe the lower Westmount area might suit you better. Food-wise, there's pretty good shopping, and the area itself is definitely upscale. It will also be a shorter drive to the west island than something further east, like Mile End or Little Italy. There are some great buildings overlooking Westmount Park that may interest you. Take a drive around Sherbrooke St., between Claremont and Greene Avenue.