This isn't just high risk your talking about Zach, your talking about compounded high risk. 

@Nathan Gesner you just have a high value lesson to everyone.

I am not familiar with how HELOCs work but they declined me saying my DTI is too high.  

Rents may be high, but where are taxes and insurance.

Also, SAAS platforms are supposed to include support and service (that's the last S), but the quality varies greatly from company to company. 

I’ve been working with several lenders for DSCR loans, but I’ve found that the fees are quite high, with minimal benefit in terms of lowering my current interest rate.

The market is at historic highs and could break at any moment.

If you are in the Tampa area and plan on purchasing there, I highly suggest you connect with @Josh Green.

@Jennie Berger gave you the whole kit & caboodle on Chicago zoning so I don't have a ton to ad, however, I'd highly encourage you to engage an architect like @Samuel Pavlovcik or @Prashanth Mahakali, both are awesome local Chicago resources.

Seems to be quite high fees but haven’t done the formal math.