I think it is by far the quickest way to generate wealth.

I think having a balanced budget would be ideal where you allocate money into buying another property and money set aside for renovations.

I don't think being a long distance landlord is as easy as some tout but full disclosure I've stayed with 80 miles of my primary residences. 

If you are able to manage it yourself, I think you will get a lot of very helpful education in real estate by spending a least a year or two doing that.You'll be able to work with property managers a lot better if you've done the work yourself for a bit, and it also helps to get familiar with the various laws and regulations you have to comply with as the owner, even if you do have a property manager in place (e.g., the new RI rental registry and associated lead paint inspections/certificates).It's up to you whether you're able to do it, but I think you'll get a lot out of the experience if you can try it for a year or two.

I don't think its as easy as people make it out to be. 

I think ability to pay and credit should both be weighed along with everything @Mike Grudzien said

I was really thinking there I'm not suppose to let the buyer see the property.

I think it likely an appraiser will value your duplex with 2 ADUs via comps with quads, but recognize there is some risk assuming this.  

I do not think anyone in Cleveland will do a good job. 

I was thinking what Dave Foster said in regards to you having troubles, especially with buying a syndication.