Anyone who can provide useful advice would be appreciated.

It has seen steady appreciation, and multifamily properties can provide strong cash flow.

I just wasn't going to give up what to me was exciting, challenging and provided so much satisfaction to work "watching the clock' and doing something I was unhappy with.  

Just to provide one example: I took a business meeting with someone who was looking for funding for a new subdivision development.

@Matt Smith - as @Christopher S. mentioned you cannot use an ADU unit in Chicago as an AirBNB as the city's intent with the program is to provide additional affordable housing. 

The struggle comes when you plan to sell, pay close attention to how the bank would treat the loan in the event you would sell.Even though its a bit more work, banks are typically open to these loans as it provides them with additional collateral in the event of default.  

These can provide good cash flow and are easier to manage than larger commercial properties, especially when you're just starting out.Also, when I was starting, I found local meetups super helpful.

My focus is on providing either turnkey-style space for those interested in temporary, infrequent use or long-term leasing for business folks who require conference room space (or perhaps event space).

On the llc side I will rent the property that I purchased from myself, and provide myself some protection of my primary residence.

Additionally, listing brokers represent what seller's provide them.