Windsor or Montreal in my case?

Hi everyone! I work remotely and I'm considering moving to either Windsor or Montreal. I'm currently in Toronto and it's pretty expensive & I'm not getting much out of it honestly.

My goal is:

1. Save more money.
2. After saving some money, trying to start any side hustle to increase my income (online or offline)

Questions:

1. For a couple is $3000 monthly enough for mid-range lifestyle?
2. Is there anything important I should know regarding life in Windsor?
3. I'll be visiting Windsor to check how are things there, any neighbourhoods or areas I should check to get a sense of Windsor?
4. Is it a big advantage to be close to Detroit or not much?

Note: I don't speak French