$55,000 in Orange County CA, - First Time Investor

[Alaska Wagoner]

Hello BP Team! Thank you for all your wonderful contributions thus far; I feel like I'm in good hands.  

I'd like to lay out my plans/concerns and see if anyone has any feedback I ought to be considering.

I'm 30 y/o, no debt and about $65,000 in savings (of which I'm comfortable putting about (55,000 into real estate at this point).  I'm not married, but will be in the next year to a college professor who had no debt and no savings, (although will be saving about 1,000/mo going forward now that his student loans are paid off).  No Kids, no plans for kids.

I have a job that pays me about $23K a year that allows me (just barely)  to write (I write!) and my fiancee and I are looking to create about $5,000 a month in passive income, so that I can afford to work less and we can travel together during the summers (which he has off).

I'm thinking that I should begin by house hacking since we are currently paying 2,000/mo in rent.  We love living in Orange County, but my fiancee only has a teaching contract for another year.  Spring of 2019 he could be unemployed, tenured in this area, or literally working in any country. If he got a job somewhere else, we would move, but I'm concerned that we wouldn't be able to rent out a house in OC for enough to cover the mortgage + savings for cost of repairs- not to mention cash flow.  Even if we did stay here, properties are so expensive that it seems hard to get them to cash flow at all, which is the name of the game in buy and hold, right?

So what's a girl to do who loves the OC, but is up for adventure?  Should I save the money until my fiancee's job future is secured (even though interest rates are going up?!) or should I bite the bullet and invest it all in this ridiculously expensive market because we love the area and at some point you just have to get started?

Much appreciation to you all, 

-A