We just finished a renovation project that we started in our name and put into an LLC half way through. 

I'll give you some ideas.I would start with your LLC operating agreement. 

You can't just buy a condo in any neighborhood and start renting it out weekly.

In these instances, usually the transaction isnt structured properly from the start. 

Before you even start spend a few hours and a lot of discussion to sort out every possible contingency.  

We can help you out with offmarket aquisition and Property Management in Cincinnati , give me a call to see if we have answers to all the woes you had with your previous PM companies you used , or if you are new to investing in cincinnati we can start from basics and help you put as well

I am working my way through "Start With Strategy" by Dave Meyer, and I am enjoying it a lot.

. - the cost starts long before any generated income.  

You should always start the call with something like this (not verbatim). 

Getting to know comps, locations, and resources in one's own neighborhood makes more sense to start.