.✅ 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.

I learned enough (in summary) what they needed to do their job in getting my funding to make it easier on myself.

@Phil SheltonYou would need a civil engineer to provide a drawing to get submitted to zoning and get a permit if it passes zoning is most common This also depends on the road - if it’s a state road forget it as it will take a year to get approved and cost a fortune - if it’s a local road process not as cumbersome but don’t expect this to happen quicklyIn some instances you may have to prepare sight distances etc to make sure it’s safe to add a curb cut

@Sophanara Khoeun you mention that you have no time as you have a 9-5 job - so, do 99% of investors!

There is a ring camera system that has a job site security package as well some of my investors use for their projects do not have internet it works off cellular connection. 

You can't genuinely expect other cities to not try to create the infrastructure, job desirability, living conditions to impede such progress.

You can't even drive by and look at a tree before you decide if it needs to be trimmed up or cut down.2.)

I have excellent credit and good paying job approval will not be a problem. 

I go through the applications and kind of number best to worse(job, salary, references) then if the favorite still wants the property, I run the reports and pay for it.

Joe its all about NPV  and rate of return for investors.. either way your going to take a pretty big hair cut out of your equity to do what your wondering about.