I definitely do not feel comfortable starting my adventure in the Oakland Bay Area (unless of course an AMAZING deal fell in my lap) because it is just too expensive and competitive here.

However, if one could pick it up for say 10 cents on the dollar, could be a gamble willing to take.  

I couldn't be more excited as my adventure and knowledge base all started here with BiggerPockets and the fine hosts and guests of the podcast.

But isnt that more of a speculation/gamble as opposed to tangible money?

It's a little bit of a gamble, but if it's a relatively small volume then you have more possibilities.Is there anything stupid about this strategy?

Think of all the adventures that await you as you jump in.Best of luck!

One thing I'm not sure of is location in this case, I suppose I could either look in a well established area and expect equity to increase through remodeling or in a less desirable area that I'm gambling will attract more attention in the future.

Got to shout out for the Santa Cruz Mountains here if you are ready for a different kind of adventure. 

Going to do some minor fixes, add a 1/2 or 3/4 bath in the basement of each unit, and start my adventure as an investor and landlord.

Playing the appreciation game can be like gambling, and if your house is really cash flowing well after all of your expenses and your mortgage payment I'm not sure if it makes sense to sell.