These are all questions whose answers will help you chart the way forward ... there is no one size fits all answer.From an operational perspective it is always pleasant to know that your building envelope is relatively efficient (insulated and air sealed); that building systems (electrical, plumbing, HVAC and communications are up-to-date and dependable) and that you have the ability to put accountability for resource consumption in the hands of the tenants.  

@Matt R.I like your chart for SF home prices, on timeline.

My last househack I gained many grey hairs.

You should see my hair!

Either or both could be forced to stop working at any point in time.Risk level on this couple is off the chart.

Just that the market combined with your state of mind tells me clean break.You can sell all as a package and 1031 into a passive investment and collect your 7% - 8% for the next 20 years but its too small for a big group without a  huge hair cut. 

Once you know where you are going you can chart a course.

The RE Cycle is just a stand chart that real estate cycles go through.

If you google search "Genworth PMI quote," "Radian PMI quote," and "National MI PMI quote" you can play around and see the variance, but again FHA is one-size-fits-all right from that gov't chart I linked from HUD.

But appreciation, in contrast, has been off the charts for like the past 10 years (bubble?).