He was just on our weekly masterclass, and has spoken at a couple of our live events.

Sure sounds good, I live towards you.

However, would I be obligated to provide housing (hotel) for the tenant due to being in a lease or do they just need to find somewhere else to live?

Each unit should easily get $1300 in rent but keep in mind I would be living in one of the units. 

My boss owner financed the current home im living in for the past year and half.

If you're willing to put your 10k into a deal and you have time to give, you could negotiate with someone who has some money and expertise to put a deal together.Otherwise, finding a way to utilize that 10k to a house hack, find some people to live with you and pay rent, gain some sweat equity, etc, and you'll be well on your way with your 2nd property!

I live in California, but am looking to purchase my first single family rental property in Memphis, TN.  

We'd live there for 1 to 2 years while saving on not paying rent and building equity.After that, my first milestone would be $10k in cash flow per month within 5 years. 

With that he can get a warrant for the guys, girlfriends' residence who lives in that town.

Where in Portsmouth did you live?