Over the years, it has gone downhill and still seems to be shrinking as far as population and business growth.

I would say this, from all of my research, any time you get above $2,000/mo rent here, the supply of tenants looking for a long term place to live shrinks.

If I'm able to shrink that living expense as much as possible, even if it doesn't "cash flow", I still think its a great investment in time and my overall wealth building ability.  

Here in Denver agents incomes are shrinking on the whole just from a nuts and bolts perspective.

if you had to bet would you say that the next 2 years will see the supply shrink even more or is there a greater chance that the supply will expand? 

If the overall size of the market shrinks (my prediction), and you already own houses, you are going to have a lot less competition for rentals overall, which will only raise your rents or at least hold them steady.Fundamentals don't really change.

Or, should I avoid Cleveland since population is shrinking and look elsewhere? 

It seems that the population is shrinking which is creating a lot of available housing.

The important thing is to look at the city to understand if it is growing (and will continue) or if it is shrinking.

You mix the shrink/swell cycles of the underlying soil and get some differential settlement across the slab and foundation cracks happen.Stucco, like brick, is a very brittle material that is unforgiving to foundation movement and cracks easily.