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. 

My tenants are psychotics or mutts, @Luke Carl would never rent to one of my tenants, and likewise, none of his tenants would have any reason to venture in to my town. 

If they're equitable owners theoretically it should be a bit on the higher side, but tied more to the profit of the venture itself.