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). 

I’m surprised the co that did the assessment won’t provide financing but it will end up being their loss.

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. 

I’m so happy to see activity from this area!

I'm sure @KimLisa Taylor and @Jillian Sidoti will be able to help you out or point you in the right direction since they are very active bloggers and forum commenters in that space.

On one side I am an active real estate investor with experience and (knock-on-wood) some nice properties.