I am sick of leaving that up to chance. I want to go covert and sneak into the town myself, and actually "lose the guards, mazing off into the streets". This is another opportunity to use that stealth attribute. And I want to pick my clothing and weapons! Why do I have to use a pole when I can use a hidden Hoplite?! And with high enough skill in stealth, you should be able to sneak behind a guard and assassinate him, making the whole "sneaking into town" think more interesting. Also, you could implement sabotage with this sort of game play. While you are besieging a town, you could sneak into the town and poison food supplies, assassinate commanders, or destroy (burn) barracks and fortifications. The game would have so many more options this way. You could also do those things as quests! Also, hoods and cloaks could add to your stealth attribute. And while you are fitting yourself to do a covert op, each weapon/armor has a notability rating. The more obviously war-like the equipment, the higher the notability rating, and the higher the chance a guard will stop you to ask questions/attack you.
While I'm on this topic of stealth missions, I may as well add this as to not create an additional topic. Escape. Escaping enemy camps, escaping prisons, etc. should all be done by the player, not by a roll of the dice. Much more fun. You could sneak to a pack next to your captor's tent, grab a knife, loose your bonds, assassinate some people, steal a horse, and off you go.