Looking at the pictures for the oil coolers, the one for 2009 baggers looks like it has less that half of the cooling area that ones for 2008 and older. Doesn't seem like it would work half as well to me. Any thoughts?

 

Your opinion has zero basis for any doubt as to what will "cool", or decrease tempretures, etc. Thermo dynamics relative to exposed surface area, and proper conduction through an aluminum structure with a HUGE amount of surface area to disipate heat.
Also take into account the designers are degreed engineers with advanced aerospace technology backgrounds who designed these coolers. They MUST be exrtremely reliable and effective to be installed on aircraft.

Explain your reasoning using a basis, not conjecture.

 

It is very lean from stock but the heat issue is easy to fix with a good tune and stage 1 big sucker. Plus you will get HP gains.