Painted the buildings and Managed the property myself.

Gather a team - a real estate agent, someone to manage the property, and local contacts.

In November I submitted my shared-housing application to Chicago’s BACP, with the hopes using my basement unit as a short term rental unit (Airbnb, VRBO, FF, etc.). 

Also consider that a deal is NOT what is advertised its what YOU make of it by negotiating, rehabbing, managing, etc to maximize its potential.

You're ability to manage is what will make or break this.

I wouldn't invest in an area just because you have a child going to school nearby.They will only be in school for a couple of years and then you have a rental 100%Who will be managing the property - Will it be you or will it be your child?

I am committed to managing the project diligently, ensuring that every aspect of the rehabilitation process is executed with precision and efficiency.I am open to discussing various investment structures and terms that would be mutually beneficial. 

In future years’ budgets, the association should consider budgeting for an Operating Contingency (funds not earmarked for any specific expense) or should consider creating a line item specifically to fund Prior Year Equity in order to bring the balance into the 10-20% range.If the board doesn't know what it is doing financially then they need a management company that does along with an accountant that understands how HOA's work.

This will be our first property to self-manage. 

Then why do you have a 10% management fee?