Hey @Stacy McGeeI ended up going with Reedy and company.

I would also get to know a reputable landlord/tenant attorney in your market. 

I already plan on forming a Wyoming LLC as the parent company that owns these other businesses and properties.

Can someone please recommend good property management companies in Gary, Indiana.Additionally, has anyone invested in Gary, Indiana?

When you transfer the properties to LLCs, speak to your insurance company/agent to have them make sure that the LLC's name is on the policy.

We went into a project with a handyman, and after 95% of the work was done, had to pull a permit for siding with an outside company, which got the county looking at the windows, which our 'handyman' didn't do correctly.  

I don't recommend going to a 3rd party company for private money until you have some experience3.

Is anyone aware of any reputable lenders doing flip and hold lending with reasonable terms?

Tim is a great resource and may be able to do some consulting to bring you up to speed, but you are still going to need a small army of vendors to get the task done.If you are set on self managing our company offers lease only services, at least that way you can get a fully screened tenant, with a lease template written by licensed attorney's and be in full compliance with renting. 

JPMorgan Chase, Nationwide, Honda, L Brands, Huntington, and Amazon are just a few of the many companies that have thousands of jobs in the city.