Starting Out in An Expensive Market

[Jacob Y.]

Hey Ya'll,
I've heard something to the extent of live where you want, invest where the numbers make sense. I happen to live in an expensive market, Santa Cruz California and want to get started investing in real estate. I am trying to develop a strategy and am thinking about flips, buy and hold, and multi-family properties. I have no experience, but I may be able to get a private loan for enough to start something in this market despite my lack of experience (I will have to show good numbers for this to happen).

What do people think: if the numbers make sense for a property, is it ok for a new investor to start out in an expensive market (average sfr is like 500k here), or should I start in cheaper markets?

If the latter, how does one start investing in different markets from where they live and work a job at the same time?

Advice appreciated!

Jacob