I offer it free to all family and friends, just a shame to leave a beautiful home empty. 

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.

Hello Friends. 

Over the past 4 months I sent out about 3,000 letters to a semi-targeted list (2% reponse rate), made 1,000 cold calls (25% response rate), had multiple investor friendly realtors looking for oportunities, and of course checked zillow/realtor daily.

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

I eco what @Brian Burke is saying above, especially on "Pref is generally a shorter term than common equity, which means you need to have a way to redeem it out.

Hi friends! 

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?

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.