My initial plan was to purchase with cash then take a mortgage out after it is rented for 3 months then use the mortgage money and add 20% more of my cash on hand to buy the next place; I could have done that to purchase 4 houses which would have my passive income at a comfortable level.  3 of the 4 houses would have a mortgage and I would have mutual funds and 1 house to cover the debt of the 3 mortgages. 

Hi @Jenny PennockI agree with @Gail Kaitschuck on trying to do a regular tenant first before dealing with Section-8. 30% of my properties cater to Section-8, but I "graduated" to this after a handful of regular tenants and once I got comfortable with the standard rental practices.

Regardless if the government can't take the money, a comfortable end of life in this Country far outpaces the amount the government provides, and in the end you are stuck with the bill.

My advice is to pass on this one if:-You are not 100% comfortable of the numbers independent of his-You do not have an understanding of your agreement together and his obligations are spelled out-Your agent has more skin in the game other than commissionsYou can always pass on this accepted bid and re bid when the property comes back on to give you more time to gather information. 

It's definitely not always easy to be comfortable right away investing further out, but when the money speaks....In terms of areas, there are a handful of good ones out there right now I recommend.

Is Kim 2.0, the recent ordinance designed as a moneymaker for long term tenants, a nightmare for landlords in the greater Bay area?  

Any suggestions on the nuts and bolts (contracts, how you structured deal, what % rate of return you offered) and how you managed the relationship to help the investor feel comfortable?

These investor see it as a safe haven, also if you read into the way the industry is designed over there, it's not the picture of stability.

I am also an architect/designer in San Diego, CA.

The lack of control over annual costs are a risk that I am not particularly comfortable with.That being said, if you are good with condo investing, I would probably base my decision on the degree of control that buying 8 units in one building gives you. i.e., if it's a small complex and 8 units gives you ~50% control, I would probably go for that.