Looking to house hack after starting from ground zero - Need any advice

[Nelson Badillo]

I am currently going through a tough time and having to start my real estate journey all over again (Previously had a couple of single family home rentals) after some changes in life. 

With that said, I am considering jumping into a house hack using my VA Loan and then repeating the process every 1-2 years until I can accumulate enough properties to help supplement retiring one day.

I am doing research on the climate of things right now in the market but the reality is I need a new place to live and house hacking seems like the best way to invest my money and lower my monthly overhead costs so I can save money. 

My question is, what is the best approach to house hack these days? Am I better suited getting into a multi-family or a single family home and look at potentially adding value somehow? I value my privacy so not crazy about renting out rooms, but I will if that is what makes most sense in todays market. I have about $50k in liquid cash and again, plan to leverage my VA loan and I have my full entitlement for it.

Any other advice in general would also be greatly appreciated. Thank you in advance for your help and insight.