Am I thinking too much? About going into the next level of worrying about the other person suffering a loss? Or I should just stop at the bowing request, and bow if the other person accepts it, period?
You request permission to bow to the Triple Jewel which is represented through a left home person.
Some left home understand this and therefore may decide to execute their own Dharma of accepting the bow on behalf of the Triple Jewel. If they execute that Dharma properly, they are not affected by your higher of gongfu because they basically do not accept your bow for themselves but only on behalf of the Triple Jewel.
Those left home people who do not understand this (representative) Dharma tend to accept for themselves. Their blessings would be depleted more quickly should their gongfu is lower than yours. It’s really not your concern because ignorant people inevitably incur losses for doing things that they are not supposed to.
Your questions are not a case of too much thinking but an act of kindness and compassion. We do not wish to make gains at the expense of other people, especially those who are weaker than us.
Having said that, over time you may come to realize that certain left people simply have no clues and do not understand the (representative) Dharma, then you have my permission to skip the bowing altogether until they get wiser. We do not wish to cause their blessings to be depleted unnecessarily.
If you have no clues yourself, then do not fret, just execute your part of the Dharma period.