The only choices you have are to pay off the mortgage so the insurance is not mandatory, try to find private flood insurance that is less expensive, attempt to flood proof the property or sell it.You may want to call your local government floodplain administrator, engineering or survey or drainage dept to see if there are any flood related improvements planned in your area, such as a drainage project, that may lower your flood risk.

Thankfully you are not telling the usual horror story associated with making a emotional decision.  

I am on the HOA board of a smaller sized Condo Association; 38 units.

@Donnersson Penna if the Condo Association is willing to do it then you'll need to work with the most local regional VA office. 

PS, I have found a few meetup groups for investors and real estate associations, and plan on attending those groups events in the coming weeks. 

I am not a fan of condo investing either as the association manages the maintenance on the property and you can at any time get hit with a special assessment.The type of neighborhoods i would look in is Albany Park, Avondale, Irving Park, Portage Park, Rogers Park etc

CBRE releases a cap rate survey that's really good.

I need to know what fees are associated with hard money lenders from beginning up to the close on purchase.

Consider joining your local apartment association (usually by extension you will be joining your state and the national apartment association). 

Due to already having 2 mortgages other places they can't get a 3rd mortgage and buy at this time.You can find out the Fair Market Rent for your area or any area in the country by going to a HUD website,  www.HUDuser.org That is the average rent figures compiled by survey of actual rents, so you can see what average rents are.For New Castle County:eff     $8451br    $10032br    $12113br    $15154 br   $1686