We would then live in one unit, use two units to pay the debt service and operating expenses, and the fourth unit goes to the lender/investor to pay off their position.

Depends on your state landlord tenants laws-Ejection is Different and more expensive than Eviction if someone is living in your house.

More for cheaper properties, less for expensive ones.

It reduces my 'expense' in the house (my down payment is equity - essentially moving money from one savings account to another), and I find that sellers are fine with it.

Assume 20% down, 50% rule on expenses, 4% interest on the loan. $1,000 to close.Purchase: $100,000Down and Closing: $21,000Rent: $1,00012 months pass and for an unforeseeable reason we have to sell the property!

Does anybody from this area or any area in general that is very expensive have any advice for somebody just starting out like me.

It's an expensive market (for the most part) but the rents are high, so it is possible to find something where your cut of the mortgage would be minimal.Adding to the areas you might like: Uptown, Jack London Square, Cleveland Heights (AKA Eastlake), and parts of West Oakland.  

I will try to track all expenses to share my whole process with you.

With $1,500 in rents coming in and less than $700 in expenses, I’m sure I could find a buyer. $800 a month in turnkey cash flow anyone?

When buying a $50k old property, most things that will go wrong will fall under CapEx expenses.