Meetup.com is a good resource for those but some of the groups will also post here on Bigger Pockets Marketplace too.

I like your post and you obviously know Chicago but a lot of what you are saying is just plain wrong.

Now I realize that not all situations will go exactly as planned but it is important to have a realistic plan from the beginning based on past results.Ivan, Hopefully this post was helpful to you in that it helped you consider different options based on your personal situation and real estate investing goals.

This was something I was intrigued about and the post jumped back to the top of the list when you asked yours. 

Quote from @Nate Sanow: Yes I own two that are near 100 years old and I will tell you they are a pain in the you know what compared to all of my post WW2 properties especially post 1980… layouts are better in the last 50 years and energy efficiency is better and I can keep going… HOWEVER to reply to the other aspect of your question, I’ve found appreciation is better with older properties in areas of the path of progress.

Letters, post cards even calls are useless to this owner class. 

Just like you said at the end of your post. 

That being said, there is a shortage of rentals in the area so a simple post to Facebook Marketplace or join the Facebook group https://www.facebook.com/groups/ElkhornandWalworthCountyOnli... 

Good listings are a people game, not anything you have at the bottom of your post.

Thank you for your post.