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

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).

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?

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.

Timing and ease re: permits in various local jurisdictions? 

Check your local zoning codes you might not be able to get permits for a multifamily if it's zoned single family.

There are a limited number of permits available in each neighborhood and there is competition from hotels and push back from the community.

permits?