I'm starting to think we are in over our heads, so I reached out to a local, trusted property management company through a friend of mine.

If it's 65%, they won't care about credit. 

Anyone care to weigh in? 

It sounds like you bring a ton of value to the platform given your past experience.As far as where to start, that is difficult to answer without knowing more about what you're looking to accomplish and how hands on/off you intend on being with your investments.Turn-key companies have tremendous appeal given the fact that they target below-market value properties, handle property management and project management.

We have 18 fortune 500 companies in the metro and the number 1 largest private company in the United States. 

If I were you, I would definitely switch to a company who can at least keep you in the loop. 

Location: Midwest, mid-size town with a number big and small companies, hospital, heavy summer tourism.

Is your "insurance guy" a captive agent (one company) or independent (able to shop around)?

Andrew and his company are incredibly UNPROFESSIONAL and I would recommend STAYING AWAY from him and his company. 

I hired an online bookkeeper to take care of that for me.