Gonzalez start application here https://webapps4.chicago.gov/eforms/aduapplicationOnce you hear back from the ADU department that your project is approved then you can proceed to hire an architect and complete the permit process.Good luck!

We are likely to hire a real estate attorney to ensure that our interests are covered as thoroughly as possible so my concerns are limited to negotiating based on a single realtor in the transaction.

I know virtual assistants would help me scale how many potential leads I can reach out to, but I don't want to hire virtual assistants until I have a proven method of acquiring good leads, that will turn into opportunities to close on Off-Market properties. 

If I want to hire property management company to manage my rental properties then why should I need license to LLC?

If you can't look at it yourself (you can fly virtually anywhere these days) you can hire a professional company or inspector to look at it for you.

I will be trying to hire a GC who specializes in this type of building to handle the whole project.  

There are websites like www.craigslist.com that allow you to hire someone to take a video of the property for you so you can take a look at the property virtually.

I'll check your suggestions out, especially if I hire help and build a team, but it's just me for now.

We concluded the guy was having a bad day.Regarding the city of Chicago being behind on inspections- We hire an expeditor for permits and inspections.

I would not be personally managing the property, I'd be managing whoever we hire to property manage.