[Fred Nerks]

... It also looks as though he had been to or spent some tme in HI before that photo with the dark boy was taken.

Any tropical location with a beach shack would do, it doesn't have to be Hawaii; although, as you have indicated, it looks familiar to someone who lived there. The child Susan saw was supposedly three weeks of age, the toddler image is one year + so maybe it's a snapshot of a holiday in Florida? I really have no idea.

Does it ever get warm enough in Boston to run around like that?

[GeronL]

That baby is holding a hammer, definitely not Obama

[GregNH]

The Palm tree and the outdoor sink would indicate a place that doesn’t get below freezing.