I have read this thread from the beginning, in order to familiarise myself with the sequence of the discussion to date as well as adding a few comments.
Re Saddleback: It is an excellent company, (with superb customer service) and, for a demanding environment (including a demanding environment where one also has to hold, or attend, formal or semi formal meetings) I can think of nothing better. Indeed, I would imagine that the 'Thin' briefcase would easily pass muster in any sort of urban setting.
Myself, I have two exceedingly elegant (in different sizes) Italian brief cases made by an excellent - but small - Italian company called 'Tuscany Leather'. They have travelled the world with me.
More recently, much more recently, I have added a Colonel Littleton briefcase - the '1943 Navigator' - to that collection, and, along with Saddleback, I have this forum to thank (especially my good friend Shrink) for drawing my attention to such excellent companies which make such wonderfully well made and carefully crafted products.
Another Italian company which offers excellent (and beautifully made) briefcases (and other leather products) is the 'Bridge' company; however, it needs to be noted that their products are rather expensive.
Re iPads, I, myself, use a BookBook cover for mine, and it then travels in my briefcase with me.