Go to meetups, attend auctions, host your own meetups, hit up EVERYONE in your sphere of influence and add value to/communicate with your database on a regular basis so that you remain top of mind.Just put in the work and try to be a better agent every day.

I expect the cash flow to be $0, and I will have to set aside some of the reserves out-of-pocket for the first year or two until the rents increase. 

In the reverse, if you increase revenues 3% and expenses 2% you're naturally going to inflate over time.

I know one thoughts are “I can sell it for more” but that increases the risk as well because if I had a $250k loan on a $225k property and values continued to decline and the mortgage is in someone else’s name - I would be like “ok let me hand the deed back and walk away and go ahead and sue me…

I'm looking for any / all advice for best practices around how and when to inform tenants about the rental increase/request to vacate.

A good agent will help you develop a strategy of the highest and best use to maximize the value to increase rents and the highest price on the exit.

just wanted to know, what strategies are you using to increase bookings?

I think arbitrage is a job and misses out on one of the wealth generators as there is no equity increase (equity pay down or appreciation).  

The way to recoup that is not to sell, but to hold and to continue to build equity while also working with his PM to increase his NOI. 

In CA MF is rent controlled but SF is not rent controlled.  12) the ADU will result in property tax increase more based on cost than actual value added   item #1 implies the property tax you will be charged is more than if it was based on value.My top advice is make sure you know the value added to the property by adding an ADU. good luck