So my understanding is if I put a kitchenette in the basement suite then It becomes an in-law suite, which can happen in a single home zone and doesn't require city's approval.

Even single professionals want two bathrooms, especially if one is en suite master.

@Michael Plante,Respectfully, does a one legged duck swim in a circle?

So I try to swim in that end of the pool.... just wasting my time and theirs. 

It might be unnecessary, but something you should look into prior to selling.Your plan isn't crazy; it isn't something I would want to do because I wouldn't want to move every 3 months but if that suits your personality then it could work. 

Best to not just jump in the deep end while learning to swim.

Is there a master suite?

Hello,I am looking at a deal that has a swimming pool.

Have you contacted any lenders to see what loan programs they offer so that you can compare and choose the one that best suits your goals?

You may also be able to find a place with an in law suite type you can live in or you can rent out, if you want the duplex like investment.