In person is better than over the phone if possible, as I have been told by annoyed or lazy clerks "NO STR allowed" as that was the easy button to get me off the phone, or if they are anti STR. 

Questions they will have is who is the owner, what experience do they have, is their key person insurance against them etc. 

The northland MAREI meeting and the main monthly meeting at MAREI have a minimal fee, or for $99 a year you can attend all of them for no extra charge - northland is in person, the main meeting is still online, both are great ways to connect and learn. 

I personally think being a landlord in Chicago is easy and I have never had an eviction. 

You are going to send your wife to personally unclog that toilet.

Networking is the key to growth...I am always down for coffee if you want to connect in person. 

These loans are based on a property’s rental income rather than your personal income, making it easier to qualify as you expand your portfolio.Networking and Mentorship:You’re already off to a great start by reaching out here!

A couple strategies that could make sense for a younger person without experience could be a live-in flip or a house hack.

Also, personalized post card size info/thank you card with the top 5 restaurant/bars or attractions in the area.

I personally will try to avoid buying a home under 1000 square feet again.