I keep a midsized compartment on my backpack just for bike related things that I would normally carry on the frame( but don't) to leave nothing for anybody to steal. That includes my saddlebag, lights, Topeak Road Morph pump, basic tools, etc. Moral of the story - I always have a pump with me and it takes up very little space, while requiring stealing my backpack off my person to steal the pump.

I have Continental tubes under my Gatorskin tires, and this combo seems to hold air extremely will. The Kenda tire/tube combo that came with my bike must have just been terrible, as I almost needed to add about 20psi whenever I was pulling the bike out to ride it (every other day or so during the summer). With the Continentals, I have not pumped up to my normal 90psi in about 10 days and I've still got about 75psi according to my gauge.