These homes may be dated, but they can be decorated to a high standard.

I had 5 houses with them that were terribly managed (placing bad tenants, extremely high rehab costs). 

Zachary,Your concerns about Cleveland are valid—high property taxes and stagnant population growth are definitely challenges to consider.

I do not judge anyone that sees a high projected return and becomes interested.  

BiggerPockets also has a calculator to analyze deals, and I highly recommend you start this as soon as possible, even if you are not ready to buy.

So, your focus may need to pivot from high rental cash flow to little to no cash flow as a rental with an appreciation upside.I would recommend taking your $150K to $200K and securing a solid equity position in something that will cover its expenses and maybe provide a small cash flow, but then is poised to appreciate nicely over the course of the next several years. 

Many of my clients are high W2 earners who are taking advantage of the "STR loophole." 

I could come up with a down payment for an investment property in a different state easier than my home state at prices are pretty high in the 300-400 k just for townhomes.

We bought a property that we feel is assessed by the our local government too high.

20% is not high for managing a STR.