Unless the downpayment amount is a factor, or unless you are adamant on staying in one of the units, you may want to shop around with some hard/private money lenders as well.

Shop around for a broker that will let you if you’re hitting a wall with your current - brokerages have different thresholds for “risk”, different minimum loan amounts, strategies they offer/specialize in.

When discussing the possibility of a DSCR loan with clients who have been shopping around, I often find that when I bring up the pre-payment penalty it is the first time they have heard about it. 

@Beau Alesi you really need to shop to compare this. 

There are many paths to success in real estate.That all being said, I should disclose I have been window shopping larger multifamily.

I would suggest shopping around for a bank or credit union that can do better.

Shop around and don’t accept the first answer you get as gospel.  

And fortunately for the environment a lot of those people are millennials who want to walk to work, play and shopping, or, at least take public transportation.

@Ibn Abney in both cases you mention, Oakland and NYC, both real estate markets were driven by the concentration of technology companies that came into the area with jobs, attracting the youth with better jobs.Chicago has............................. no technology companies wanting to set up shop there and the number one city in the US where people are leaving the area.Without technology companies wanting to set up shop in droves, it's a dying city in my opinion.  

I would be happy to grab lunch with you and talk shop, but I will be out of town this weekend for a wedding.