Hey Kris,
I'm new to investing as well and asked quite a few seasoned investors this same question. The best answer I found was that although properties will more easily cash flow in other markets, as an out of state investor, you miss out on a lot of the value-add and with it the returns when you invest from afar. To invest out of state, you often have to rely on other people (agents, landlords, turn-key, contractors etc) to add value to the project (find it cheap, rehab it on a dime, tenant screen, manage it) and they get the rewards, while you are left with the crumbs. Not to mention the lack of appreciation in many of those markets. Then, just one flight to fix a problem could devour your cash flow for the year on a single family. On the other hand, if you invest first in your own back yard, you learn the tools to add more value in future out of state investing and could probably accumulate capital through appreciation and forced equity in your own back yard, large enough to do bigger deals that make more sense managing from afar. For example, if you bought a few small multi-families for a few years and benefited from the growing appreciation in Portland, you could take a HELOC from those properties and put a 20% down on a 20 unit property in a cheaper market and place an on-site property manager to run the whole thing. Or better yet, you could build a reputation among friends and family and gather funds to invest in larger deals out of state down the road. Best of luck in whatever you choose!