Hello all, my wife and I have been in our current home for about 15 years.

It's easier just to continue with the current PM rather than finding a new one and going through the transition, but I would start looking around if I were you. 

@Devin Basile Current LLC's should not be part of this. 

I'm trying to be sensitive towards the other unit at the duplex paying the market price currently and what it looks like renewing with them.

The region's population, currently around 3.2 million, is projected to grow significantly by 2030.

An example like this is https://www.zillow.com/homedetails/1377-14th-Ave-San-Francis...Another example is https://www.zillow.com/homedetails/1949-23rd-Ave-San-Francis...This house was sold for $1.1M (way under current SF market), simply because there is an protected tenant inside.Just want to pick up everyone's brain and experience here.

Every year, you are giving this guy more money in the current deal.Finally, since you will be acting like a bank, then you also need to vet this guy - credit checks and references and background checks.

The MTR rent is currently lower than the LRR rent even 1 year after the quota went into place.  

Websites like Zillow often have owner information, especially if the property is currently listed for sale or rent.

You buy it based on its current cash flow.