I scour for MLS listings each day to see if any good opportunities pop up and I'm also slowly training my mother and sister to drive for dollars.

You will have negative cash flow on that property especially considering the opportunity value of your equity.

As I am doing my research in the Oakland market, a lot of the math is starting to look slim in terms of cash flow so I started to study properties that could possibly be renovated with condo conversion potentials as a value add opportunity.

I️ don’t know if this is a huge opportunity or huge nightmare!

There are places int he Midwest however, that will give you bigger cash flow, but potentially more problems regarding repairs (older areas) lower class neighborhoods (depending on how cheap you go).Indiana, Ohio, etc has some opportunity.  

What's worse is that the value of the apt moved up from approximately $1 Million at the time to about $2.5 Million.The reality is that my friend was not only losing in Cash Flow when taking into account his living situation in NYC but he also lost opportunity cost because he had the chance to buy a Condo that was very similar to the one he rented.

A lot of deals are never listed and taken directly to known buyers so you need to be on their radar.There's also some syndication opportunities around Indy if you are looking to scale.

Is anyone aware of any part-time opportunities where I could learn from an experienced investor and offer digital marketing expertise or other skills in return (social media, website design, ads, etc.)? 

Born of the desire by folks to provide passive investment opportunities that also qualified for 1031 treatment. 

Let’s connect ;) I️ acquire a few good buy and hold opportunities every month.