All three are great markets, but extremely different cities. 

I took a RAL Academy course in the past, which teaches you how to run residential assisted living homes and this seems like a golden opportunity, especially with demand being extremely high with the aging population. 

I own a seasonal business here and due to lack of employees I don't have enough cash to cashflow my business through the winter (or its going to be extremely tight).

A lot of people told me Poconos are not a cool place to go but the area is extremely hot, homes for sale disappearing in a week. 

Looks like you're in a good area to be in since the Midwest is doing extremely well with REI right now.

I looked at this and thought it was extremely high.

We are new to Canada and extremely worried about having a thin credit file in Canada.

As a tenant, it would be disappointing to see my neighbor using the washing machines and being reminded you have to leave your home to wash your clothes.

I may know couple of people locally here in Chicago who might help too.I've used Upwork to get tasks done like that and honestly been extremely helpful!

This situation sounds extremely high risk.