There are some habitability/improvement upgrades you could potentially take on that would allow you to remove the tenant without cause, but there's still a lot of grey area around that since the law is new. 3.

Maybe you live in a touristy town where AirBnB is highly profitable, maybe there is a high demand for student housing, maybe the local hospital needs furnished apartments for their traveling doctors etc. 

I travel 4 days per week and I've run into tremendous challenges managing remotely.  

Some questions I am trying to answer are:What demographic of travelers are staying in these listings?

I currently have several cards that combine to offer me roughly $3000 worth of free travel every single year that I can either use immediately, or stockpile it for my big world tour once I retire.  

If those lots are not counted in your Certificate of Zoning, you could appeal that they are wrong on the count (but you'll need a municipal lawyer to represent you) or you could go buy a $500 travel trailer and put that on the lot and see if you can get a city approval for electric hook-up (and if not, you're back to the attorney again).

I would be traveling from Toronto, Ontario with my wife.

I would think that the tax's on the additional income would make it a wash.In addition you might (I'm not 100% sure) lose the 250K tax free deduction when you sell your primary residence, as it could be argued that it is ... well, a rental property and not your primary residence.When you have multiple properties and travel between them, it makes sense, not so sure on a single residence or everyone would be doing it and it would be all over the news, internet.

I am looking to build my portfolio enough so my wife and I can travel and have more family time with our son and soon (october) daughter.

Willing to travel, move around and be in multiple markets.