Flood insurance can be really high. 

What type of insurance do I need to get as I will need to evict the person first and then do some rehab to make it a rental?

The train goes through Gary, not so nice, and quite a bit of the lake front is heavy industry around there.

HiI own several multi family buildings in Central / North Florida and for example on an older duplex I pay $700 a year for insurance, which I feel is a good deal. 

Even legendary billionaire investor Warren Buffett, with all of his endeavors into energy, insurance companies and holding sizable stakes in companies like Coke and Wells Fargo, still calls his own home his best investment ever.

I've made many improvements to the property to insure it was properly secured and to prepare it properly to become a rental property.

Holding costs are things like mortgage payments, taxes, utilities, insurance, HOA fees, and anything else that pops up while you own a home.

I have many years experience in the building materials industry working at Home Depot and interstate building materials.

Arguing the probability of a city of 212k can immediately replace a city of 1 million + (Austin is about 1mil, Bay Area is 7) as a leader in any industry is certainly not the point of this post.

As long as your careers are in the same industry/field for at least the last 2 years you should be fine.