Make sure you talk to them at their level to nurture the relationship and not be adversarial.  

I talked to them earlier this week and was wondering the same thing. 

They also appreciate honesty and transparency so they can make decisions fast without any surprises.Some of the top skills that you can focus on are:Comping: Knowing your comps inside out is a must.Negotiation: Being able to connect with sellers and strike a good deal is huge.Networking: Relationships with buyers, agents, and other wholesalers are invaluable.Also, Get to know your local market being able to talk the talk in your area will help a lot.

Have you talked to him about it?

Happy to connect and talk about options.

Also when you are under contract and get condo docs, make sure to read the meeting minutes (for the past year if available) they will indicate if there are any talks of an upcoming special assessment (which you don't want).

Hey @Mordechai Chaimovitz - It sounds like you are talking about Chicago's NW side because there are definitely tons of areas in Chicago where a 2 flat can cashflow well.I know for me buying on the nw side was critical to my personal well-being and life happiness. 

But if you are just buying a home that you will keep as is...that's something that just about all of us do pretty easily.Feel free to reach out directly if you want to talk it through some. 

I would do what @Mike Grudzien says and talk to a knowledgeable attorney on this.

I was talking about your Realtor vs Property Manager, here Realtors doing property management need a separate property management license