One of the biggest things I would do is sign outdoors, weather permitting (might be difficult if it's raining, with paper documents and all).

The biggest challenge we faced is booking them since they were pretty busy.

That being said house hacking is still an incredible tool and just because you don’t cover the full 100% / can’t quite cash flow positive you are still mitigating the vast majority of your families biggest expense while getting into an awesome business, building equity, having a shot at appreciation etc!

Thanks in advance for your time and discussion.The biggest unknowns right now are rent growth and financing.

@Jonathan Farber The biggest risks to doing this are below. 

What's the biggest point of improvement?  

The carpets are my biggest concern due to the horrible smell, do I need to attempt to clean them or can I just go straight to replacement?

This is a significant expense if the property is not separately metered, which is rare for heat costs which is the biggest expense 3.

As for the Ramsey market, I just filled an Anoka vacancy on edge of Ramsey in 2 days, literally, and my biggest problem is the continuing stream of applicants for the unit, lol. 

Cash flow is my biggest concern.