He didn't have any equity to pay an agent and he couldn't pay them out of his own pocket.

And in every locality that makes up tenant-favorable protective policies like the ones you've laid out, OC always, always benefits.

The cash flow isn’t great as a rental and it has major equity built up.

I have a rental condo in Little Italy in San Diego that breaks even monthly with $200k equity in it.

I have a rental condo in Little Italy in San Diego that breaks even monthly with $200k equity in it.

However the final buy price was not very favorable.

There are a lot of places in the country where you could get $500/month cash flow with a portion of that equity. 

I would recommend putting some sweat equity into both properties and force some appreciation, then in 6-12 months you could either refinance the equity out of the new properties or do a HELOC and use that for another property or 2.

.- forcing equity or rehabbing altogether?

I have done a live-in slow-mo flip on my first residence and built quite a bit of equity.