Real estate investing is a team sport and at different points in the game different players will play more important roles.

I do not see any of those scenarios as likely and therefore see poor/negative cash flow at max LTV refi continuing for some time.  

The problem comes into play when those milestones are not good indicators of one’s progress towards a goal.

A good landlord wants to do reasonable business to have continued tenants.

I’m continuing to invest in real estate while also helping others achieve their real estate goals.

Assuming the Oakland rental market continues to remain stagnant/competitive with newer buildings going up, is property appreciation the only way to increasing wealth with my building?

I’m building a tech solution that should drive more buyer leads to an agent’s pipeline. But to build this I will need access to NAR APIs. Is there any developer here who can share their experience building with the AP...

If a tenant is constantly paying late and there seems to be a clear sign of struggle in finances, wouldn't I be doing a dis-service by offering the tenant to renew their lease and continue the vicious cycle?

It's all about who is dumb enough to continue to pay that kind of money for a system that already gouges people in a way that even the Gambino family would disapprove of. 

My suggestion is to continue being active on BP, get out to some networking events and seminars and also educate yourself through books and podcasts.