I rented a bike last week while on the road, and flatted three times. What I learned:

• CO2 is nice for a quick fix
• A pump with a gage is very, very nice for a fat boy to make sure the tire gets pumped up enough
• Foldable tires are far easier to get off and on the rim than wire bead

So, on my return home I plan to put the wire bead Gatorskins on my bike and put foldables on my wife's to replace her wire beads (so it's easier for her), put a CO2 system in each seat bag for the quick fix (rainy, or cold, or dark, or late, etc). Finally, a pump with a gage so I can make sure I get enough air in there to not pinch flat.