It can certainly be rewarding, but you must due solid due diligence to control risk. 

@Brook RiemanI think you need to run the numbers and compare to another investment types..

Condo appraisals require comparable  properties outside of your project.

As a fellow west coaster, I understand how difficult it can be to find local returns that compare to some of those found in other parts of the country.My favorite part of your whole strategy ... training up your boys and teaching the next generation ... those memories and lessons are worth more than the paint and plywood. 

Looks similar where it has huge 'swings' compared to the other times it went down a bit.

@Dean Letfus I would say both markets are pretty comparable in the types of neighborhoods etc...

The assessor looks at comparable sales to come up with the value of your property, they don't actually look at what's been done to it unless there is an addition.

Investors are always looking for agents that will "put up with our antics" so if you're patient and willing the rewards can be great. 

Should we be more aggressive in purchasing SFH for better tax advantages compared to passive MF investing?

Real estate and stock market investing are not comparable..nor are they alternatives for one set of goals.