I would suggest speaking with a HELOC provider first.  

Appreciate if you have similar experience or any suggestion. 

The height of each unit is about 8ft I believe.let me look up the sqft I believe it's a standard sized lot for chicago so about 3000 sqft Neighborhood is starting to see some nicer units rents are all higher but it's leans more low income I have a contact that is going to ask the alderman if I could build a separate unit and have the original as an adu architect suggested extending it as they believe it would be easier to get approval than a separate home

I highly suggest teaming up with a broker who you'd want to build a relationship with and truly understands the ins and outs of different underwriting guidelines for DSCR loans.

I also found that in order to have a successful STR in our market you needed something to make your property stand out, game room, hot tub, creek, lake etc.

If you are looking for ROI I would suggest South Florida or Tampa area. 

My suggestion would be to contact a couple of Independent Agents (they handle multiple insurance companies) that write in GA and get quotes. 

One day the maintainance guy came at the property and discovered standing water in the basement.

Would you suggest hiring a property manager or run it myself ?

I'm open to any insights or suggestions on how to structure this project in a manner that benefits both parties.