For the last 7 years I’ve been in the car business working my way up through the ranks and am currently in a finance manager role working with banks and lenders getting folks approved for car loans.

The key is to avoid turn key companies that don't allow for a finance/appraisal contingency or require the buyer to make up the difference. 

I think there's a fine line between being a landlord and having a personal relationship with your tenants.

The process is probably going to take a little time: you'll have to apply for the permit, then (likely, depending on the nature of the work you did/are doing) have a "rough" inspection (that the contractor will take), and, then, after finishing the work, have a "final" inspection (that the contractor will also take) to close out the permits.

@James Heacock Here are the key things to look for in a turn key company and what to avoid.If you're going to go the turn key route, in general, the ones to avoid are the ones that: Don't allow financing or a finance contingency (it can be a good indication they are selling above market value)Don't allow for your own independent property inspectionAre not realistic with their pro forma's (i.e. they don't include vacancy or maintenance projections or use unrealistically low vacancy factors)Require you to pay for any renovation upfrontSell only in cheap. low end neighborhoodsDon't accurately represent the neighborhood/property classificationDon't have consistent rehab standards for all propertiesDon't provide a scope of work for the propertyCan't provide references of repeat investorsRequire you to close before a tenant is in place

This is your chance to renegotiate based on inspection findings. 2 week before closing : schedule final utility readings, title search should be performed, and you should get homeowners insurance squared away. 1 week before closing - financing commitment if you’re getting a loan or mortgage. 24 hours before closing do a final walkthrough of the property. 

If you went into a fine restaurant and ordered steak but they brought you lobster and you have an allergy to lobster, would you get on a forum and complain they served you lobster?

Well Chicago can be a fine market to in nvest in...many people do.

Or buy and close the property under a finance agreement, then find a buyer? 

A fine based on what grounds?