Another amazing find! I am continuing some research based on your initial marvelous work and will likely post something in a day or two.

You asked about the other Obama painting:

Although I haven't yet taken enough time to thoroughly examine this work, something obious pops up - the pine cones.

In the occult, pine cones signify occultic knowledge and also the pineal gland, or third eye.

Thus, in this painting I surmise that the artist wants to show that the subject has either developed the ability to open the third eye and/or is privy to occultic, secret, knowledge.

I can notice a few other things, but would like to examine a higher res picture first. Do you know where I can find one? I have done a reverse image search on this in Google images, but nothing turns up.

And where did you get the info that the painting's subject is Obama?

Do you know the artist's name?

Thanks for this amazing video and post of yours! A lot to dig into here...Interesting to say the least.