Assuming the area checks out, I’d rather buy in a high price area that has little to no cash flow rather than an area that has cash flow but lower price.  

One thing you might do is sell your more expensive properties and buy less expensive ones. 

Quote from @Alex Spivey: I want to start renting as soon as I can so does anyone have adviceYou want to find a place to rent and occupy, or you want to buy an investment that you can rent to others?

Buy a 2-4 unit, close to home.

I've worn three hats in the seller financing world (as a property buyer, as a property seller offering terms, and as an investor that buys seller financed note). 

Hey Somesh,I was wondering if you ended up buying a property in Cleveland and if so, how it’s going.I’m also from Toronto and looking to invest in Cleveland.  

So if you see any let me know and ill buy it! 

-------------------------------------------------------------------Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

The more information that you have out there the easier it is for people to find you, if you want them to find you.I almost everyday wear my "Rick Buys Houses" shirts with my phone number on it. 

when i buy dirt and do the horizontal these deals can take 2 to 3 years 2 years to get through approvals and horizontal  12 to 18 months to build and sell.. thats a 20 to 25 lot project.