Currently, I am leaning more towards Sacramento as Hayward is still a bit past my affordability.

Lean startup4. 

I would suggest, if you are leaning towards a SF house hack Hendersonville would be a good area to look into.

I'm fairly indifferent to the ratio of assets in the stock market vs. rentals - I see the value and challenges in both and don't lean strongly one way or the other. 

Not sure if they are in your numbers already but the 1960 property will likely require more ongoing maintenance and repairs than the other, so with only the information provided, I'd lean toward Property 2.Beyond what you wrote, I'd compare the communities.  

One of the reasons we decided to sell is because it is over an hour away from where we live and we could not source cleaners etc, so we have been leaning more towards purchasing more multi family.

@Steven Wilsoni generally tend to lean toward your line of thinking, if you can make that kind of cash flow within even a 5 year range I’d say it’s worth it.

Our mortgage lender gave us the option to waive the appraisal - however, we have a clause in our contract that if the appraisal comes in over 10k low, our price goes down to appraisal +10k.So, we are leaning towards ordering appraisal anyway, on the gamble that it comes in low and we get a discount. 

Whichever route I go, I am leaning toward using property management to make it more sustainable. 

I am leaning towards holding it as a rental after living in it a few years but with the improvements I have already completed it would be a very painless and easy flip.