I agree on that it’s predictible that OBL wanted to bring down the leadership, if only because he read some books sometime that said it was a good idea or something. What I just can’t get is how did he thought that Obama was prepared at all.
I don’t think that Obama’s “preparation to lead” had much to do with it — only that Biden was just as bad, if not worse, in terms of ‘competence’.
In WW2 the western allies toyed with the idea of assassinating Hitler. Ultimately it was decided that having Hitler as the one calling the military shots for Germany was advantageous to the allies. He was an amateur.
What the allies couldn’t predict was who would replace Hitler since his succession was rather ambiguous. What worried Churchill & Roosevelt was that the Wehrmacht would simply seize power (the way the Imperial General Staff did in WW1 by shoving aside Kaiser Wilhelm). They couldn’t take the chance, so Hitler was not assassinated.
Consider what might have happened had Hitler ‘designated’ some incompetent, non-entity to be his successor. I think that the allies would have whacked Hitler in a heartbeat.