I don't want to waste anyone's time and I don't want to start off with a bad reputation. 

Not great, but not bad either. 

On those websites, a listing that old is either the owner just trying to see what they could get or it’s a bad property (either economically or physically).

I need major expertise - since I am still getting started in my real estate investing career.

On one hand you want to be humane, but on the other hand bad tenants can make your life miserable chasing them for a few hundred bucks.

I remember in real estate school the instructors warned us "buyers are liars" and that your career is much better off with listings rather than showings for buyers.

@Bob Starlin When Mark Twain said 'Good decisions comes from experience and experience comes from bad decisions' he must have been thinking about investing in MF-we will never know for sure.

The rent will need to be a 'fair-market' rent, i.e. is it equivalent to what a non-related party would pay, or a similar rate as other SFR's in the area are charging.Additionally, for further proof of intent as an investment, it is never a bad idea to have a lease agreement with your tenant, whomever they may be.

Go get a job first.House hacking without funds is probably the most difficult career.

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.