If I’m luckily and low ball I could get $100-$200/month.

They are only meant to get you in the ballpark and it sounds lie the ball park is $2500 - $3000.

In my experience I have had some builders/manufacturers push back against this process but if they want the business then they will typically play ball. 

And it does not work every single time, life throws you curve balls.

I have the opportunity to make an offer on a property in 44104. I know this is historically a rough area but I have heard rumors that is is up and coming with the $$ the Cleveland Clinic is putting into their expansio...

Usually after walking through the property he is able to give me a good ball park figure of what the renovation should cost barring unforeseen issues.

Step 1 in marketing is getting as MANY eye-balls as possible to see that listing.

I know or know of people in your same position (executive level tech experience + capital) who have done well in this business, and also ones that have imploded in a spectacular ball of flames. 

Id love to connect it anyone willing to share some advice or guidance to help me get this ball rolling. 

Yeah, house hacking is a great way to get the ball rolling.