Luckily the market had moved in his favor so he was able to sell and didn’t lose that much money.

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Very interested in the Cleveland/Ohio market in addition to a few other cross-border cities closer to Toronto. 

How is Cleveland market? 

I'm assuming you're not looking to turnover the tenant, but your rent appears to be way below market.

Get it under agreement for less than asking price and offer to bring the loan current and have them carry that loan.The way I see it is they are just getting MLS properties under agreement - the last five I looked at had been sitting on the market for more than 150 days (overpriced) because the payoff of the loan would not be satisfied at lower price point. 

There are very few markets that cashflow with 100% leverage.

The one big caution I would have for investors on the design is don’t make the room size too small.

During this 24-month period, the property must be rented to another person at a fair market rental value.After the 24 month period your sibling could convert it into a primary residence.

The strategy may change, but every market can work.