Generally, you should be banking on 2-3 year but tracking #s monthly to ensure that everyone is staying on track.

I stay off Tapo Canyon a lot. 

Average tenant stays 2-3 years.Thanks!

They seem to always stay rented with no problems at all due to the price, location, and them being pretty nice units.

I fear you’re going to find that your minor gain is going to turn into a major gain because of the depreciation.Depreciation recapture many times a nasty surprise

Our goal would be to make sure the house that we are not currently staying in would be used as an air bnb. 

Now this being said, should I prorate rent for them for a day (I feel like I don't really need to), or should I just recommend that they stay out of the house for a few hours, and I tell the painter to make sure all windows are open and the fan is on while he paints?

I was down there  earlier this year networking and looking at properties, and after hearing lots of bad things from Calgarians about Windsor, I must say it is a beautiful city with great cash flow potential, making it our #1 pick to invest in if we stayed investing in Canada. 

Honestly surprised it's lasted this long. (~$5k)2) It has front basement windows/sunroom.

.), length of stay, etc.