@Bryan Cavellier, You can 1031 with any US property including Guam, the USVI and ...drum roll- The Northern Marianas Islands (go figure but I actually had a realtor from there in a class of mine recently) into any other US or one of those territories.  1031 is a federal statute so it's applied the same in all locals with just a few variations state to state at the state level. 

Sell one of these in a few years and use your accumulated wealth (appreciation)  to buy a STR at that time.

Instead, you must invest in a purely passive way, such as a syndication.Second, real estate is a tax-favored asset and investing in a tax-favored asset through a tax-deferred vehicle is a bad idea. 

Now I am interested in growing a little into the single family realm in a neighborhood closer to my home.  

Similarly, if you put several Class D tenants in a Class A 4-plex, what do you think will happen to the property?

I am attending the 3 day event in a couple weeks.

I'd do it again in a heartbeat.

Even if OP can complete a purchase in Cleveland with $23K, aside from valid concerns others noted about reserves, is the risky asset in a distant market really the best place to invest?

Some will prefer to stay together in a large Vrbo property.

This guy claimed to have hundreds of homes which was a complete lie and then drives idiots around the Philadelphia hood in a party bus for thousands of dollars.