I reinflate my tires before each ride, just to be on the safe side. I technically don't have to if I'm riding two days in a row. I'm about 136, my bike is probably around 25 pounds loaded, and I run my tires at about 105-10 for the back and slightly lower for the front. (My bike has 25s on it.)

I don't think most road bike brakes will take anything wider than 25s. And they won't take 25s comfortably (you have to deflate the tire most--if not all--of the way in order to get the wheel on and off). I don't have any recommendations--I'm still running the same tires that came with the bike (Kenda Kriteriums). Probably will go with something like a Continental Gatorskin...at least an all-weather tire so I won't be as worried about getting caught in the rain!