If I am riding locally, I take the small inflator...
If I am going on a long trip, I throw this small compressor in my back pack. When I ride from AZ to CA, there is a long 60+ mile stretch of desert highway with no services. I figure if I develop a small leak, I can inflate the tire with the compressor, go 20-30 miles, stop again re-inflate and repeat until I can get to a service station.
Again, I think it would depend on the circumstances and distance you are riding.
*** Note *** the $20 bill is just there for size reference and comparison.
In the end, the last flat tire I had; I just called AAA and had the bike towed, as I was local. I had my girlfriend pick me up in her car for a ride home. She started to give me grief about motorcycles in general, no spare tires, etc. etc., thinking quickly, I suggested a trip to a local ice cream shop and she quickly forgot about harassing me about the bike. Oh the power of ice cream to quiet an angry woman...