A $300/mo cash flow on a 285k house is objectively a good deal and not one that I would be keen to part ways with for cash.

You need to develop a keen sense of when they are "sold" so that you can then transition the conversation away from "selling" and instead move it towards engaging them as a client.There are TONS of FREE resources about how to be a better agent online.

Happy to make some connections if Chicago interestsAre you more keen to get cash flow over appreciation?  

Wife and kids aren’t keen on moving into a multi-family or a big fixer upper but we are still on the lookout for something nearby that we could move into and then rent our current house.

Personally, I'm not a huge fan of Boston and Brookline investing and am also not too keen on condo investing unless you are on the Board. 

I’ve talked to an agent I’ve used my personal homes and they didn’t seem to keen on what I am looking to do.

Just sit on the application if you aren't too keen on renting to them (hint - I wouldn't be).

Keen question here.  

People who fake a disability to get their pet into housing, or on a plane, or into a public place, do a great disservice to people with real disabilities who have a real need for a service/support animal.Most fakers will back off if the landlord has keen knowledge of non-discrimination law and a procedure in place which requires appropriate documentation.

Keen question here.