Really happy to have found one site that addresses so many aspects of my new venture!

I'm definitely inclined to #3 as I got into this venture as a safety net and somewhat stability (otherwise I would just do REITs), but pulling in potentially bad tenants would be contradicting.

Unfortunately, I just basically hopped on my new house deal and opportunity to get a 2nd home and decided to try landlord venture on a whim. 

You can even find way cheaper properties in these markets if you decide to venture in to D grade neighborhoods.Your best bet as a California investor would be to look into out of state honestly.

Smaller deals are typically accomplished via Joint Venture or a private loan type arrangement.

Is he a joint venture partner or is he charging you a fee for service?

If cashflow on that single house looks good, I might start adding properties and/or partnership, to start a small RE "venture". 

I would like to try flips to fund more rentals eventually but I have a good thing going now and want to keep learning what I’m good at before I venture off.

Joint-Venture with a local investor

We are looking to venture over and expand to the Chicago market and would like to chat and discuss with investors that reside in Chicago who have some experience in that market.