Already done this to myself -- it lowers your self-esteem enormously.
I used to do exactly this, but I created whole backstories and personalities for my "hats" so that they would be more realistic to other people.
It might be more accurate to say that pretty much everything, including what we call biology and physics -- humans are the ones codifying it -- is memetically selected to be learnable by humans. Not that it all develops towards being easier to learn.
May I ask how many people any of you have seen walking around entirely barefoot, as opposed to wearing minimalist footwear of any kind?
To be perfectly honest, at the time I simply planted my face on the table in front of me a few times. I was at a dinner party with friends of my mother's; I would have sounded extremely condescending otherwise.
That is what happened to me.
The lack of this knowledge got me a nice big "most condescending statement of the day award" in lab a year ago.
I have attempted using this in more casual decision making situations, and the response I get is nearly always something along the lines of "Okay, just let me propose this one solution, we won't get attached to it or anything, just hear me out..."
One could attempt to fight that by reducing the number or frequency of M&Ms eaten over a long period of time, essentially weaning one's self off of extrinsic rewards.
I think you enormously over-state the difficulty of lying well, as well as the advantages of honesty.