I am not sure how saturated that market is (both with properties and managers) but the first question you should ask yourself is is the market underserved and how can you improve the current offerings to local owners? 

Is there a pre existing loan with that bank with either of you?

How much do they want you to to pay, to pay off one of the mortgages (or both of their existing mortgages)? 

I managed STR with my sister twenty years ago before Airbnb existed.

I have also really considered medium term rentals, however it seems that the market is somewhat saturated as many rentals have been dropping prices significantly when I look through Airbnb.

Have you considered tapping into your existing rental equity for the down payment?

If the Owner wishes toterminate the agreement during an existing tenancy the owner will be held liable for payment ofmanagement fees for the duration of the existing lease as well as a $300 + GST cancelationfee.

But if you know what you're doing in finding the properties and want a fixer upper, it's doable.I will say that the multi-family rental market is pretty saturated here though. 

Pete and Clearwater still work well for mid-term rentals despite some short-term rental saturation.

My buddy sold for ~$500k over its existing use value and no contingencies and did not even convey existing tenant’s deposit.