I know it's difficult to find a house hack that cash flows right away in today's market, but if 60-70% of my living costs could be covered, that'd be great.

It's pretty difficult to get an investment mortgage at the moment. 

Right now the market isn’t that great but I could see us looking to purchase a multifamily duplex however, in the current market, I’m finding it difficult to be able to have one tenant cover the cost for that property to break even.

They are not allowed in certain master planned communities.Summerlin, including Sun City Summerlin▪ Town Center▪ Skye Canyon▪ Cliff’s Edge▪ Symphony Park▪ Grand Canyon Village▪ Las Vegas Medical District▪ Providence SquareAnd these restrictions I find would be the most difficult for you to overcome - A short-term rental license does not provide authority to violate any common-interest community’s covenants,conditions and restrictions (CC&Rs).

Unfortunately many of the improvement costs do not deviate greatly when you’re renovating a lower cost property  in a particular market compared to a more expensive property  in the very same market which makes it difficult to absorb the improvement costs in some areas.

It is not guaranteed money, the properties are often not in good condition, and CMHA is difficult to work with.

Well you can but it makes it more difficult when you have zero cash to work with (ask me how I know!). 

Are you finding it difficult securing financing for your deals or are you looking to connect with borrowers that are?

I've been involved in the Indianapolis market for 6 years and I can tell you that those low end properties don't perform unless you are local and hands on and even then it's pretty difficult.

The moral of the story here is that vacancy is so low right now, especially in Tampa, that it is very difficult to get flexibility with your lease.