I live 30 minutes outside Chicago and I'm attempting to start a second career as a real estate investor and agent.I've been a full-time career Firefighter/Paramedic for 13 years and I want to find another career to transition into so I can leave the fire service in 8-10 years.  

You're asking the right kind of questions.My understanding of the Tax Reform act is that the interest deduction limitation is $750k for a first + second home.With that said, it may be advantageous to purchase the property as a second home, then place it in service as an investment to capture the advantage of a lower rate and deductibility.The catch is that you'll have to keep the property in your name vs. holding title in the name of an entity.

Would using a flat fee service to get it on the MLS be discouraging? 

@Adam Q Berry-Huff,My two cents would be to focus on the spread you are making between your current debt service and your current cap rate. 

Each unit has 200 amp service currently. 

Yes, there are investor-oriented real estate brokerages that assist clients with the pre-acquisition analysis and support services you seek.If Metro Atlanta is one of your target markets, I'd be happy to refer you to the same brokerage I refer my own international clients to.

Each unit has it's own electric service - tenant responsible.  

As a Property Manager, I provide a limited service that I refer to as "Tenant Locator."

To completely defer the gain on the rented portion of the duplex, you need to acquire property that is similar or related in service or use to the original property that costs at least as much as the amount realized upon conversion (e.g., insurance proceeds).It does not mean that you have to actually spend the insurance proceeds related to a rental portion of a duplex, the replacement property must cost as much the proceeds but can be acquired via a mortgage. 

The service we use is called ´' Imail'' which is provided through my brokerages services , CRM , Etc.