New RE investor strategy - invest OOS for cash flow or house hack in HCOL area?

[James Hunt]

Hi Bigger Pockets!

I've been here for a while reading up and am excited to make my first post.

A bit about me, I am 30 currently making a great salary in a W2 contract role that I will likely remain at through this year, after which I expect to look for a more permanent role with a lower base salary, however likely similar overall once benefits are accounted for. I have about 50k liquid and plan to get closer to 80-90k by the end of this contract. Currently living with my girlfriend/no kids in San Diego. I was born and raised here, and have an elderly father who lives nearby, so I know I don't want to leave. However, this is a very difficult real estate market to get into due to the high price to buy.

I'm currently bouncing back and forth between the thought of investing out of state into a turnkey property that cash flows (still whittling down the markets, but have been researching a few), versus house hacking a duplex here in San Diego. I do really love my apartment/neighborhood and would certainly have to move to a less desirable part of town if I were to house hack, but I also know that if that's the best route, it's better to do it now, rather than when I may have kids to think about.

What are your thoughts?