It's one of my favorites because I don't have to spend any money to do it. 

I have an RE agent license even though I don’t work actively as an agent, hence I know what overall prices are in the neighborhood.

If you and your wife file a joint return then from the federal perspective you and she (or rather the tax return that reports the activity of the properties - all of them both from during your marriage and before your marriage) are one and the same tax payer.

We are from out of state, so our agent will need to be actively involved in our due diligence process.  

If you take SD, you dont itemize, but the expense related to rental activity has nothing to do with itemize deduction.Your rental income is taxed if you have net rental income. ( Rents- expenses- depreciation). 

Plenty of activity in South Shore today. 

@Barbara Hlavaty I think first of all, you have to figure out for yourself whether you want to be active with this next investment or passive?!

For example, while you could use such accounts to purchase real estate, you could not transfer any real estate that is owned by yourself, spouse, parents, children into the tax-advantaged account.There are also some instances in which such accounts can be taxed, such as when investing in an active business or when using leverage.For a list of companies compiled by BiggerPockets, see: Self-Directed CompaniesFor more compliance and strategy, see: The Self-Directed Investor  

Especially interested in connecting with anyone in the Chicago Western Suburbs who is active in local real estate clubs/meet-ups. 

Getting active in your local REIA, hanging out with similar like-minded investors and building relationships are key.