Haiti and the Dominican have remarkably different political histories - Haiti has a lot more awful dictators in its past. They're poor comparisons. Toronto and Detroit are probably even worse - Detroit is an industrial centre whose industry rotted out around the same time as it was levelled(metaphorically) by race riots and people fleeing from them. Toronto is a financial and cultural centre whose primary challenge is that they're short a freeway or two and the commute times are bad. If you want to compare Toronto to anything, NYC or maybe Chicago are the obvious candidates.

As for a close cross-border comparison, I propose Seattle and Vancouver. They're close, similarly sized, and culturally close. You can also look at smaller examples(Sault Ste Marie ON/MI, Niagara Falls ON/NY, etc.), but it's harder to get good data from those due to scale, even though they are even closer in geographic and cultural terms.