Many of has some of the same, or similar, concerns, Old-Duckman. Your list is not debatable; your concerns are your concerns. I would not, nor should anyone else, try to sway you to a smart. But, should you decide on a smart you will be in for an adventure. Sure, a big part of this car will be the discovery of its capabilities and its shortcomings, but what else is life about if not discovery and adventure? Plus, that stodgy Honda hybrid will be there if you decide to sell your smart later down the line
By the way, I have sold my Prius (nothing like a pre-sale on a car that I can keep until my smart arrives) in anticipation of taking ownership of my new car. The smart will be my only vehicle.
Good luck in your decision-making process and welcome to the forum!