But I’m glad I did it and hope it’s smooth sailing from here on end. 

It's not a get rich quick thing nor will it give you much cash in the early years, but after several years the sails seem to blow off of it.  

I started my STR using Airbnb exclusively and its been smooth sailing.

Once I did that, it was smooth sailing.

Whereas Cleveland has doubled tripled or much more in the last 10 years, even East Cleveland which is where we are trying to buy everything, but there is no inventory, BTW you are not going to get anything near Case Western, that boat has sailed :) We are looking/buying just east of there, 

That boat sailed three years ago. 

You will probably do fine, but it may not be smooth sailing.

The only ship that won't sail is a partnership.

However It might not, so the plan is to in 4 years move down to the keys, give up the high stress life, start some low stress, low volume law practice (that I can practice from my boat while fishing a sailing), and use the modest income to live off of while using the extra passive income from the houses to buy more and more and more real estate, and eventually retire off of it. 

It's not pretty and it's no always smooth sailing, but there are those that take it very serious.