I will stay in the property every couple of months for a weekend or so but then would rent it out on airbnb when I’m not at the property. 

I think personally it makes sense if you're staying at a good rent level and can buy a multifamily house to generate cash flow.

Now this was two years ago, and the rent has gone up to $1250 with 2 of the 3 students staying with the house and splitting the rent even with the price increase.

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.

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.