And that residential department will often not speak to the commercial department.

Yeah interest rates currently make it really difficult, as houses are often cheaper to rent than to pay the mortgage + taxes on.

But ultimately all tenants leave, all debt comes due, and you're going to need to backfill it, so who is that, what pool of tenants could you consider?

Simple is often better, especially when starting out.

Profits do not justify their effort even with the ADU addition in this case typically not being hands off .Here is a list of things that make ADU additions a less than optimal RE investment but the value added and starting with tens of thousands negative is a big one that needs to be well understood. 1) The value added by the ADU addition is often significantly less than the cost of adding the ADU.

Often, I have cash sitting around between opportunities and have looked all over for a bank that will hold the cash in some kind of interest-bearing account.

I know several investors who choose to represent themselves, but they often end up netting less than they would if they had an agent.

One of the most important skills you didn't mention is networking, which you are obviously doing well at too.I'd recommend connecting 1:1 (zoom, coffee. lunch, etc.) with a couple from the BP Chicago community or better yet check out some of the local meetups: https://www.biggerpockets.com/forums/521-real-estate-events-...Make friends with the meetup hosts...they will often know whos who and can help you make the right connections.Regarding your license, I think it's a great idea if you have the time and are going at it with the right intentions. 

Often, these agencies also list upcoming, or pre-foreclosure, properties that are in the process of being foreclosed.

. - Often, you can pay a tenant to do the cleaning.