The time question first. How can days and years count in Purgatory where there is aeviternity, no time existing.
While time never exists in eternity, time still exists - it exists here on earth. I always thought that time will end at the end of the world, at which time all the souls in purgatory will be released from purgatory, joined with their bodies and enter heaven. Not necessarily in that order. I guess I base this on, I think it was Our Lady of Fatima who when asked about a certain soul, said that soul would remain in purgatory until the end of time.
We can choose who gets the indulgence, if that person is already in heaven then God can apply it to whomever He wishes.
When one loses a loved one they are left questioning for the rest of their life.
It seems there is plenty of room for discussion on the subject of indulgences. Anyone like to begin? I am sure many will benefit from any lost or unknown theology on Purgatory, especially me.
Yes, we never know "if they made it" in this life. For example, my parents and closest friends /relatives, the ones who kept the faith, received the Last Rites and had the Gregorian Masses said for them, yet I still pray daily for them. It may seem redundant but if they are in heaven then all is good, if not then hopefully they will be soon - either way we did / are doing our duty and all is good with us before God in that department.
I will often offer prayers for mom, dad, etc., Myrna, etc., "and all the souls in purgatory that I know or who know me." Sometimes I add all kinds of people, like all trads, all clergy (some by name), relatives and ancestors, and so on - in order that I get first dibs on who gets the indulgences.
In the end, the more souls we can help, the more help we will receive from them!