Newbie to Realestate (San Diego) Area

[Renaldo Hill]

My name is Renaldo, a Midwestern native, and Active Duty Sailors of (9) years, currently stationed in the San Diego area. I have zero experience in the marketplace, and have recently been introduced to Bigger Pockets, and have been avidly listening to the podcast. As I listen, and begin to do my own research, I am finding that San Diego is a tough area to move in -- given that property values are so high. I am currently looking at a 1,052 sqft 2/2 condo with an attached 1 car garage and two additional (dedicated) parking spaces, priced at 365k with a 235 monthly HOA in Escondido, CA.

This property allows me to utilize my Veteran Affairs (VA) home loan, so I would be able to go in on this with zero down, zero points and a pretty competitive interest rate, and a monthly payment around 2400. Now, this home on the interior looks like an extra from "That 70's Show", so upgrades are needed all around. I have zero experience conducting in home repairs, so more than likely I would be on the hook for paying a contractor to do it for me. The problem that I foresee with this is, not knowing what the ceiling on this place would be. Is tossing a few thousand dollars in upgrades, going to yield a bigger payout when I go to sale the property in the future? If I rent it, will I be able to do so at a cost that would give me positive cash flow in the foreseeable future? Or should I set my sights on nearby Arizona, Nevada, or even back in Ohio, and Michigan (where my funds go a much longer way)? At the moment, I rent a room from a friend, which allows me to be bit riskier in the market place as far as being on the hook for a vacated rental and such.

I know this is a lot to spew out in a first post, but I figured if there were some ears that are willing to listen, offer guidance -- it would be here.

Thanks in advance for any assistance that is sent my way.