355 fob/immobilizer (New question - I hope)

Is it possible that you can get the fob & immobilizer closer to synching by attempting to start the car? I have had the following happen to me at least twice. After pressing the fob button 3 -4 minutes, I get frustrated and attempt to start the car with the expected nothing happening. Then I push the button a couple more times, chirp-chirp, and away we go. So, did I accomplish anything, or did I just work my way to the head of the queue?

I try to alternate fobs every couple of weeks, so it doesn't seem possible that one can get that far behind, but they seem to. What is some poor schmuck going to do if he puts one key away for a year?