It seems like a natural succession for a large multifamily unit owner to also own their property management company.  

The more adversarial your approach the higher the risk in increasing the cost.To determine the boundaries, check the legal descriptions of the properties in both of the deeds.

Increase profit and maximize tax savings

Using the capital I made from those closing invested in larger yellow letter campaigns, and incrementally increase my budget from there. 

I moved from downtown Toronto in 2012 because I saw the soaring RE prices and the cost of living increases.

The exact nature of your legal situation will depend on many facts not known to me at this time.

You may want to look into something of that nature

Is there anything else I should consider when assessing this increased risk?

I own a SFH in Los Angeles and am thinking of making some upgrades-1) opening up a retaining wall that leads into the backyard and install a sliding glass door2) adding a 10x12 wood floating deckMy questions are:1) How would I calculate the increase in value for these upgrades?

Let a mentor-student relationship grow naturally.