DocuSign does charge a fee, so have the broker you worked with on the purchase handle it.

I have also started courses to obtain my brokers license in WA.

And never sign an exclusivity agreement with a broker....bad idea.

Any reasonable MF broker knows the expectations outlined above. 

They will often be between 50 to 60% when roof, windows, water heaters, heating and air,etc. starts reaching end of life expectancy and has to be repaired to extend shelf life or fully replaced.Many times some brokers do a ( if buyers don't ask then don't tell ) kind of thing to get stuff closed and make their money.

Avi Reichman I would advise to connect with a Broker or Real Estate Agent here on BP from your state or your local area.

By putting your rental on MLS, it will be marketed to brokers who are incentivized to find someone qualified to fill the vacancy.If you'd like to handle that on your own, you can certainly use Zillow and get plenty of traffic there as well.

Any recommendations for 1) brokers who could do the BPO (ideally I bring the broker to ensure Independence); and 2) an Illinois lawyer who will know the mechanics of setting this up?

They're not brokers but most claim to be direct to seller or one away from the seller. 

As a list broker I know that people  will definitely call to complain if they have the feeling that you are in with Big Brother (maybe you're too young to get that reference)You might talk about this the same way you would with almost any audience: home ownership can be a big responsibility with the expense and maintenance....