I suppose I do something like that with certain plants, such as brassicas, which I sow when the flowers on last year's plants are opening.
Mainly though I keep a note of planting dates each year, plus extremes of weather and results, so I have established a pattern for here, over the years.
I agree that in some instances wild plants do know what they're doing, but not always. Some plants do seem to get caught out by late frosts, damaging winds etc. In the end, I think you just have to trust your judgement, and maybe try several sowings to be sure of good results.