I understand the importance of knowing specific areas well, as this would make my life easier, but I also think that with the technology we have nowadays (maps, street view, market analysis, etc), some research and a rigorous approach, this is something that could produce very interesting results.I'd like to know your thoughts, investors!

Am i approaching it wrong?

Obviously my approach is just my view and you should decide what is best for you.  

Best time to approach a bank is when they sell out to another bank, change of management or when a new one is going to open.

You are elephant hunting with a BB gun, you need to get out of the jungle and learn real estate.Your questions are so vague they can't be answered without writing several books.Land is always valued with the market approach unless it yields income without improvements, then the income approach may also be considered. :)

Many prospective Buyers are looking at sale comps and not income approach on these types of properties when making purchases.

I'll take the opposite approach.... 

However, given that they've also given us a formal appraisal of their value, it's actually also another piece of leverage to re-approach the owner. 

In New Orleans I was on the board of one of our neighborhood organizations, and when approached by Whole Foods they let us know there were requirements for parking, average income, and traffic. 

I went into the house yesterday and there will be lots of deferred maintenance as the owners have taken a very hands off approach to landlording.