And now he owns multiple high rise apartment buildings.

Typically, appraisals which don’t involve a sale/purchase price will be more conservative.When the Identical house to yours actually sells, then you could try again.

There is always risk involved

We want my wife to be equally involved in our new side-hustle, so are there any introductory type of books that you would recommend to help my wife get in the right mindset for running a real estate business?

Hi Bob,When purchasing apartments/multifamily, there are 10 main reports you want to obtain during the due diligence phase (between contract and close):Financial document auditInternal property condition assessmentMarket surveyLease auditUnit walk reportSite surveyProperty condition assessmentenvironmental site assessmentAppraisalGreen reportMuch more involved than due diligence on a SFR.

Keep applying that pattern in your life, in whatever you get involved with, and I'm confident things will work out the way they should.

Notice how all these hypothetical individuals are involved in business before anything else.

My plan is to take the money from the sale of my Oakland house and reinvest it into multiple properties to start off my investing career--I'm just not sure where and if I should go SFH or multifamily. 

Speak with multiple companies.   

Yes, I'll be sure to get multiple bids