I am hoping to begin investing in Real Estate by house hacking in the near-future.

Shall we start with the demographic that rents houses?

Or did you mean you'll be renovating the house so that other third party assisted living services can rent from you?

I have a friend who is an agent that is looking to assume my VA loan and buy the house off market, so that I can avoid paying fees and commissions.

I would highly encourage you consider House Hacking.

People don't like the idea and have the mindset that they would always prefer a homeowner in the house.  

We are a low volume housing provider.

House hacking right now in many areas will be at a loss, but less of a loss than owning something with no income coming in on it.

Repair budget set at 40k or 20k for each house.

I vividly remember the countless hours spent driving to and from remote locations in rural Manitoba, alternating between early BP podcasts and Jim Rohn recordings.Over the next two years, I adopted an extremely frugal lifestyle, enabling me to achieve a 75% savings rate, sold my custom truck for a used Toyota, traded my new home in the burbs for a duplex (house-hack) in a challenging neighbourhood of Winnipeg where attempted break-ins were commonplace.