I've got a few hundred clients in your exact same scenario, they live in markets where rentals don't make sense whether it be from a price or laws perspective.

Some of those guys made hundreds of millions in a couple three years.

Right by clark and Devon just few hundred meters out of rogers park into edgewater new builds going into 1.4s.

There are quite a few out there - the Community will provide you connections with hundreds of other investors who are looking to do the same thing you are.  

The only tech company based here that I know of is Neighborly, which has several hundred employees.

They do everything from framing, trim, painting, roofing, siding, flooring, cabinets, etc. and they can tell you when the plumber or electrician didn't show or did something wrong.

I don't know that there is a much bigger vetting process other than if they can pay for leads, but correct me if I am wrong.I have been on here for ten years and sourced hundreds of leads without ever asking for a single thing because all I do is show up and answer questions and add value.

Light rehab, paint, blinds, fixtures, and paint cabinets.

for example when changing cabinets, addressing trim, door pulls. hot water tank replacement: place a pan under it.  

You are going to most likely have a stranger hang on to several hundred thousand of your dollars.