I am betting your gonna find a lot more friendly amicable persons than shut doors. 

He's been the only person I've communicated with in the past.

.✅ More Control – You’ll personally handle tenant screening, rent collection, and property upkeep, ensuring everything is done to your standards.✅ Stronger Tenant Relationships – Being involved directly allows you to build rapport with your tenants, which can lead to better communication and longer leases.Cons of Self-Managing❌ Time-Consuming – Dealing with maintenance requests, late-night emergencies, and tenant disputes can quickly become a second job.❌ Legal Risks – Chicago has strict landlord-tenant laws.

Personally, I think I would stack some cash for a year or so while I did this. 

If you wanted to fund a portion of the down payment would you suggest a hard money lender, personal loan, etc.?

Personally I prefer single family homes around that median price because that's where the most demand will be not only for owner occupants but renters as well.

We've not met in person yet, but know each other.

I know this is an old thread.I'd like to get a more recent opinion of these apps.I think the DFD options is very interesting.What we want to do is endorse one of these for our Real Estate Club in Greenville, SC and have a contest for our members to see who can find the most deals with the software.Maybe try and get a rep from the company we choose to come and speak at one of our in person meeting and also negotiate a longer trial window if possible for our members.

Are you building for pure investment purposes or are you looking to use some of the space for personal/personal business use?

., the appraisal for 5+ is at least $2k-$3k) and the financing structure by lenders because Fannie/Freddie don't generally buy loans for commercial properties.So, for you personally, the biggest driver for the type of your next property is probably going to be the amount of a down payment/equity you can put in the property.