I'm thinking about how I would use the space once I move out.Option 1: I could do a basic finishing (to make it live-able) and when I move out, make it a part of the first floor unit rental or Air B&B itOption 2: Alternatively, I could “go big” with the basement and try to make it a three family (obviously this would require approval from the city).Option 3: something else I haven't thought ofI'd appreciate your thoughts.

I can never get a hotel room there, and Air BnB’s are scarce, so this tells me there may be more opportunity in the short term space.  

This implies that using the chimney vent to run wire is a no-no; each system needs to be independent of any other subsystem in the building.NEC 300.22 specifically covers wiring within spaces that handle exhaust or environmental air.

As such you will need to have the air ducts cleansed and new filters. 

I am also renovating a cottage in Bobcaygeon which I will be doing Air BNB with a partner.

With tenants currently residing in this property, I am going under the assumption that major repairs wouldn’t be immediately for each unit, but that is up in the air until I do a walk through.Is it out of the ordinary to request information with regards to tenants this early in the process?

What type of fix-up work is needed for the home (i.e. floor work, plumbing heating and air conditioning, roof repair, etc)?

I am Active Duty Air Force and Big Blue is moving us to Tampa Bay, FL next spring.

Banks or insurance typically require air sample outside as baseline.

Did you do a search for your neighborhood for any Air BnB listings to see if anyone slipped through the cracks and find out how?