The woman standing close beside the kenyan wearing the numerous lei is of interest. However, it's a concern that the man supposedly the kenyan appears to be the same height as Stanley Armour Dunham, standing beside him. That image has been discussed at length numerous times, there is considerable evidence of tampering. The girl you refer to as 'Anna' was identified as ANNE/USA on this website, scroll down to REMINISCENCES
In the beach photo it is clear the woman in the front is Filipino (not Indonesian, Japanese, etc.). Less clear is the woman in the back. But With the INS indicating their is an estranged wife in the Philippines in their letter this is a path worth following.
THE ON THE DOCK IMAGE; The woman in the black dress in the foreground has been tentatively identified as a Hawaii resident, however, there are opinions that she was added. There is really nothing conclusive about that image unfortunately.
The question remains, is the woman with the kenyan on the Dock, the same as the woman identified as ANN/USA at the Nachmannof gathering?
Barak Obama and his friends at a party hosted by Arnie and Suzie Nachmanoff, in the early 1960's, in Pearl Harbor, Hawaii Lower Photo; Taken in Hawaii in 1961 at Arnie and Suzie Nachmanoff's house (Pearl Harbor): from left to right: Kiri Tith (then Cambodia), Kitaichi (Japan), Marda (USA), Ichiro (Japan), Suzie Nachmanoff (Host, USA), Dave (USA), Kunio (Japan), Bob (USA), Rajapakse (Sri Lanka), Barak Obama senior (Kenya), Anne (USA)
It is very hard to say if it is the same woman. But the hairstyle is similar. The beach/lea photo is better than the the sitting photo and both are not great.
My comment on the woman is that they are of Filipino race - not necessarily nationality. And yes the woman next to Obama is also of Filipino heritage.
As for photoshop - it is hard to tell with these supposedly old photos that have been scanned, resized, cropped, etc. They are small and poor to start with.