Thank you for your question!
Let us remember that “less suffering” as “more happiness” is a subjective state which varies according to the role to play.
Let us say that you are married and that your wife is not in the knowledge. As a consequence you suffer, because you have to put up with many things to keep peace at home. Are you having less suffering than being by yourself all the time and feeling lonely? Every role is distinct, different and there is no way to compare them. We cannot assume that “most of the karmic accounts have been settled” but we can safely assume that following the maryadas and “getting” the knowledge will be easier the second time, because the Sankaras are there already.