Hopefully along the way your properties appreciate, you pay down debts  (mortgages) from operating income, and you get market appreciation on what you can rent each unit for - giving you more income each month. 

Made good money for a while then the market turned and he lost a lot of coin ...  

Most buyers don't have the money to come in with to pay down payments, plus commissions in this market, so I don't expect a lot to change.

I know the market fluctuates and that can be a factor, but generally speaking.

Evaluate the rental market in your area to determine the optimal configuration for maximizing rental income.The choice between using cash flow from your current house to cover expenses or pay off the mortgage faster depends on your long-term financial goals and risk tolerance.

My worry is that the property might fall into probate or tax auction once he passes and someone who knows someone will get the deal under contract before it reaches public offering.There is a real estate agent in the area that gets about 85% of all the listings in the micro-market, so she is farming these properties constantly. 

I know Austin; I don't know other markets.

Off market deal that I was approached on by someone I have done deals with in the past.

San Jose is obviously a tough market to start in for cash flow - are you looking at any remote investing markets/strategies?

Our town just did a revaluation and got close to 100% but the market constantly changes and prices continue to trend upwards meaning the 100% valuation is likely already not accurate.