This has been a good thread. I have learned a lot. Everyone's situation is different... here is mine.
I only bike in a pretty populated area (Minneapolis/St. Paul and suburbs). But, I bike with my wife and two sons. My sons are very young (4 and 7). Young children make bad scenarios worse very quickly. Last week, I was out 10 miles from home. If I had a flat there, it would make for a pretty bad day, but not endangered anyone's life. Still, if I can avoid pain by planning ahead, I will. Also, I can see us biking even further out... ideally.
Within 250 miles, my CCS2 has had two flat tires. The rear tire exploded within the first 3 miles (they mailed it with a pinched inner-tube). It was like a concussion grenade. The front tire developed a slow leak. I could ride it a few hours, but it would deflate over night.
Also, in general, many of the bike tires seem to deflate in about 2 weeks. I just blow them up right before we ride. Still, I know there is some risk, and I'd rather avoid changing all those inner tubes.
My local bike shop is under 2 miles from my house. Changing the front flat tube was $19. At that rate, I'd rather pay someone else to do it, as the tube alone is about $10 on amazon. The back tire was a bit more like $27... still worth it, as I have a rear hub. I generally don't have to wait. Maybe i'm lucky. There are many things I would like to learn if time were not an issue. But, it is.
Here are my takeaways.
1) I can call AAA for a bike flat. I did not know that prior to this thread. We do own a AAA membership. I googled, and it appears I can do this in Minnesota. I always have my cell phone with, and it's usually charged.
2) I bought a can of this:
Hutchinson Fast Air Puncture Repair and Inflation System
3) I'm buying this pump:
LEZYNE Alloy Drive Bicycle Hand Pump Compact, 90 PSI, Presta & Schrader, Bike Hand (seems the right trade-off between cost and quality. I didn't like spending $60 on a pump I'll ideally never use.)
4) I may eventually buy a snake tube, but they are relatively expensive, and while they are an easier solution, they aren't easy.
5) I should bring my bike lock, even if I don't plan on locking up my bike.... as a last resort option, in case i have to ditch my bike for a short bit.
I think that's my plan. It's not fool proof. There are still risks, but in life you should plan for the 80% and not the 20%.
Thank you all.... feel free to provide any additional suggestions, if you like.