@Jacob SteeleI believe the biggest issue is what happens in 12-36 months when those roommates move out and you still have 25+ years of a mortgage?

I have been passively looking at the small multifamily homes for a house hack, but the biggest hurdle is finding one in an area we both are comfortable to live. 

You will get this biggest bang for your buck using this approach than putting down 20% OOS.  

The biggest question in doing the deal is there is currently a tenant who is under section 8 housing.

It requires maintenance, especially on that tax front since taxes are one of the biggest, if not the biggest, expenses.

I've had numerous people come out and give their thoughts on how to work around the location and ventilation issue, but they all come back to the same issue: the balcony is the biggest ventilation impediment.

As far as I can tell, the biggest commercial RE that are doing fine are the following:1.

I just sent you a PM.The biggest challenge is this market is the low inventory fueled by a large demand in the region from retail buyers.

My biggest fears with properties like these are making allowances for big ticket expenses when cash flow is good but small. 

The biggest drawback for most people is that you normally can't get into the property to have a look before your purchase.