I'm curious if you have considered approaching local non profits that might want a private partner.

Or your can buy multiple properties with small mortgages.

I sold a property last year that required the owner to get a certificate of nonconformity to be a legal two family.

Here are a few simple and free ways to learn: Go to real estate meetup groups, attend open houses and speak with the agent there, inspect FSBOs (for sale by owner), walk your area, and speak to people tending their yards.The idea is to engage with other people and ask, Ask, ASK questions about their experience with the local market.Some other ideas: find a home inspector who will let you tag along in a property inspection, and absorb what they are looking at and why.Your mindset and enthusiasm for learning about real estate will open many doors for you.Good Luck!

But properties that are always right to hold forever are few and far between.

The neighbor didn't want us to build there and he ended up buying the property.

This property is a shared unit so we don't want a locksmith to change locks, then the roommate is locked out.

I am getting 3 estimates on the property in the next week but could also do some of the work between my dad and me.

You'll find a ton of kind, supportive, and helpful people here.Are your existing 7 properties currently in Chicago? 

Just because the home is renovated, does not mean the market in that area will reflect a higher value for the property.