I originally purchased this house to be nearby my grandmother in her last few years but realized quickly that it was a prime area for short term rentals as there are no zoning rules or permits necessary etc.

The costs involved are about $100.000 all in (permits, engineering, architects labor , materials ) - I’m thinking that would be a better long term Investment than another SFH . 

Here's a link to the CSLB license check.https://www.cslb.ca.gov/OnlineServices/CheckLicenseII/CheckL..One thing though...in my 33 years of contracting, I've had dozens of illegal permits pulled under my number leading to major problems.

You should answer with, anyone over the age of 18 must apply and be approved to be formally added to the lease and permitted to move in.

I'd also check if renovations were done and if so were permits pulled? 

I do owe him 5k and told him the checks were ready for pickup but still no response 1- You hold that 5k until…2- Review the details in your contract, specifically Scope of Work, release payment descriptions3- Review contractor default or termination clauses or language in contract4- Review permit status with municipality, if permits were pulled.

What general contractor recommendation have you used in the past that can pull a permit with the City of Chicago that you recommend?

You need to pull a permit, then the Contractor has to take down the coping and bond beam a couple feet, then core holes in the pool floor (so it wont ever popout of the ground).

The land has been cleared already and we're about to start permitting process.

These investment properties are being built to Indiana residential code and are approved at each stage of development by the city and city permits.