I think there are different nuances in different techniques, so in any situation there is one technique fitting better than others.
My advice for training this would be a sort of restricted randori: One attack and a few techniques which are close together.
E.g. attack is shomen-uchi, then doing only ikkyo-ura, irimi-nage and kote-gaeshi. Those three techniques are very close in the beginning of the movement, you are stepping off the line and turn into uke´s back side. By doint the techniques you can discover the nuances, the little diffrences.
And then of course many variations of the choice of techniques.