I'm sure that in general, properties in the Loop are probably class A and Englewood is class D as they are essentially polar opposites but with our city being one of so many 'hoods there's a lot of variation in the middle...and I'm feeling a bit stuck!

Not legally required, unless you signed paperwork with her. 

He'd essentially then be acting as a property manager as well.Any advice would be appreciated,Drake.

If you have the properties only in your name or your husband's name, then you can essentially raise that limit to 8 (4 for you and 4 for your husband) properties.

Agents are getting lazy and casting wide nets, expecting buyers to find their own properties so the agent can do the paperwork and close the deal.You should fire her and look around for an agent that does take an active role.

You essentially have a property that didn’t cost you any money, just your time.

The cash flow is very high ($1070/month on $52,000 investment), deprecation is very fast even without accelerated depreciation, but there is no large upside on the backend of the investment because the asset is essentially plywood, a computer chip, and a cash dispenser. 

If you use a GC, this will easily double since they have to float the money to pay the subs, fill out a mountain of paperwork and also have some profit in there. 

There are plenty of other properties on the MLS that could be similar in rehab costs to these city owned properties with less paperwork headache.

For example, the lawyer will own the property 50% themselves or find another Costa Rican to own the other 50%, then (hopefully) create paperwork that doesn’t allow that Costa Rican to steal the property, (although this has happened on many occasions including the lawyers themselves stealing the property, so I'd be very careful who you choose to "partner" with).