Where do I start to talk with someone about investing and what would make sense on paper for me to do this deal? 

I would start there to make sure you can STR the place.It doesn't make any sense to rent a single room at a single room rate when there is a whole, empty house involved.

Current Situation: I am trying to househack a house in Cincinnati as I have 4 people who have agreed to live in the property that I buy.

Would love to connect with agents and other people who are familiar with the house hack model in this area. 

You have to be very selective, and you need a long-term outlook to make sense a building in Chicago.

It appears you’re talking to the wrong people.

I hear that some people had trouble with Hospitable and VRBO.We haven't tried Hostfully yet because there was no free trial. 

The sub to community trains their people to call properties on Zillow and get connected to agents and ask them to make a sub to offer.

When vetting Wenatchee on paper I know it doesn't look the best but the numbers are skewed.When Googling the population of Wenatchee you're going to find that it only reports 35,000 people.

So many people will no-show.