A fun experiment: rent or buy in the Bay/ Surrounding Areas

[Jesse Snyder]

Hello All,

My First post; how exciting. After pulling my hair out trying to figure out what to do in this situation on my own, I figured I'd reach out to a community of people who have been there and done that. Any potentially insights are greatly appreciated.

I work in SV 3.5 days a week and come back down to my mom's house in Seaside for the weekends and my days off. My mom's landlord has passed and our 3/1.5 1200sf house in a subpar neighborhood (seaside is similar to Oakland/LA with gentrification slowly creeping in) going for $460k. Complete with drug deals, fireworks, and grow houses on every corner.... I digress.  You wont find rent for much cheaper than 2gs for a 2 bedroom, most are not dog friendly. (Deal Breaker)

Most houses are going for 400k minimum in C/B neighborhoods. I am self employed and have a nice SV income, and want to make a good investment. I do not plan living here for the rest of my life. Ideally I'd like to retire at 35 and move into a house that I've made a vacation rental. I'm an avid surfer, so I should be able to rent out most places and allow the occupants to pay down the mortgage in a couple untapped vacation markets. 

Overall I have no debt, very little expenses, six months to move, and a want to invest. What would you do if you were in my shoes?