If you had a good "investor friendly" CPA he/she would write off enough to give you the deductions you need to help counter your W2 or 1099 income.Reason I say sell the first home is even with $40K in equity its not worth it to do a cash out refinance.

Purchase price: $170,000 My friend and client bought a condo in streeterville.

Also, I’m considering working with a real estate investor, property manager, or an investor-friendly brokerage—do you think that’s a good idea?

So I think about my dear BP friends, do you ever use it?

Hey Dee, BiggerPockets support is super friendly and quick on their feet. https://www.biggerpockets.com/contact-us#customer-supportScroll down to the bottom of the page there's a contact form you can fill out and they typically respond in a few hours. 

Montgomery county is a rent control county and they are very tenant friendly.

A friend has a two-flat investment property, with both units currently rented out.

Hello all, do you guys know of any investor friendly Title companies in Chicago?

@Shawn McMahon I will echo that getting connected with a good real estate broker will make things easier, but meanwhile the Redfin.com app gives you the next best access to MLS listings, and is a little more user friendly than the MLS Portal.  

We lived there for 2 years while renting the other unit out to friends.