She said there's practically no way for the city to expand its territory.

I’ve only been doing buy and hold deals so this is new territory for me, thanks for everyone’s input and if you guys have anything else to add I’m all ears!

Many who do this business remotely have developed some solid systems in place that alleviate the need for a physical presence, along with some "boots on the ground" as well.

This is spread sheet territory. 

or since you know the bay area, these increases just come with the territory and you will it is still a bargain?

Usually they'll search for you online and if you don't have an online presence it'll be harder to build trust with them.

For the last 6 months I've been self employed with my online company.I finally have some real money and I really, REALLY want to finally pull the god damn trigger.I have no friends with real estate and seems like anyone ive approached locally doesn't want their territory stepped on, only interested in selling their (cash flowing at least) flip. 

My concern is someone familiar with the territory might just give me a guesstimate based on when the property last traded Plus or minus any appreciation.

Oh boy, you are entering into dangerous territory when you combine feelings with business.

With all that said this territorial possession is about on the same playing field as the US was ten years ago during the great depression.