There's a reason that people try to buy properties off-market and that is because you can find sellers who care more about terms than maximizing returns.So start with a conversation: you already presumably have some rapport since it's your landlord and you've spoken before.

How is Cleveland market? 

Look at their marketing strategy.

In Cleveland you can find below market rental ready duplexes that require minor repairs (keep in mind that discounted properties come with their own challenges).

Study the market.

The more effort you put in to make your home stand out in a (maybe) already congested market, the higher the chances are that someone books your furnished rentals over others.

Just as bad as the posts you see from time to time of the grandchild wanting to work out creative financing to buy their grandparents house below fair market value.  

The stock market is up something like 80% of the days long term.

How valuable is this location in that market? 

Years ago I bought houses for $25k in my market.