Hey! I have been successfully renting out 3 rooms in my single family home while living in the unfinished basement for a little over two years now. I have only had to change over tenants one time and each three rooms ...

Hey! I have been successfully renting out 3 rooms in my single family home while living in the unfinished basement for a little over two years now. I have only had to change over tenants one time and each three rooms ...

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

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.

With one million dollars and picking up the houses while distressed and refinancing you can build an extensive STR portfolio. 

Also look at how much the house has increased in price-if it has increased a lot, you may want to sell it to avoid paying capital gains which will kick in if you sell it a few years down the road.

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.  

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