Would obviously have preferred to use a third party but this accomplishes exactly what I need - a birds eye view of the profitability each month without have to re-enter operational and tenant data into my own system when the property manager is already tracking this information. 

Critical features for me: calendar mgt, manage client communication, communicating with team (i.e. cleaners), supply/operations checklist per property, and vacancy reporting. 

After nearly 3 years of operating history, I'm concerned that the properties are not performing well enough to warrant continuation of the venture, and I'm considering selling.

Study up on warrantable vs non-warrantable condos.One idea I think for a fresh grad, is to find a great RV park operator. 

Reason I ask is there are companies out there who will tell you that you can get business credit but in order to do so you need to be an operating company not an investment companySo just asking so you potentially could avoid spending good money and time chasing a ghost

It is Fire TV but I find it pretty easy to operate.$60.78 Hoobro storage chest - https://www.amazon.com/dp/B086JFXB5F?

If you've transacted in hundreds of transactions over the last two years and have 15 employees how are you funding the current operation? 

We do have our retirement accounts, brokerage accounts, HSA accounts, etc… and will continue to invest money into those respective accounts for retirement purposes.With above stated, I would appreciate if  anyone can give me an honest opinion on how to start my journey as in what would be the best operation plan/strategy given my current situation and assumed future plans before partaking.Thanks in advance for anyone replying and assisting in the matter.

If the unit does not comply with local codes (like proper egress, zoning approvals, safety standards, etc), it cannot be legally rented regardless of how it’s marketed.The safest course of action forward, would be to bring the unit up to compliance with chicago's zoning/ building codes before attempting to rent or advertise it. 

But it's what my thoughts are and determines how we will operate and spend our money.