If you want to be able to fly out, Calgary or Edmonton are your best bet. 

I would say your best bets is a gym as a tenant amenity or a community room that tenants can rent for family functions, parties, etc. 

Understanding my customer, I bought similar properties to what they were currently renting.This strategy is similar to how national retail chains operate: identify your target customers and provide what they want.

I bet no more than 5% of the population is in high fire risk areas.  

@Daisy RuizTo echo @Michael Baum, I have not seen or heard from many people operating STRs in Chicago.

Strategic planning and phased upgrades are critical to balancing renovations with ongoing operations.

Strategic planning and phased upgrades are critical to balancing renovations with ongoing operations.

Strategic planning and phased upgrades are critical to balancing renovations with ongoing operations.

Strategic planning and phased upgrades are critical to balancing renovations with ongoing operations.

If you're hoping to be a co-GP and learn to both operate and raise capital then I think investing money in a good education system is probably money well spent.