I obviously can't speak for Bhikkhu Pesala, but here are my thoughts on it!
it is through constantly being with someone that you know them as good or bad, if you see someone being generous and can see they are a good person you may wish to emulate the good qualities of that person, so by simply being who they are they are encouraging others to be likewise, this was something the great disciple Kasappa favoured doing.
there may also be people who are good, or not all that good yet encourage openly others to do good, all these people are encouraging us in different ways, one has modesty, not liking others to know how good they are, and the others may be trying to hide how bad they are, or not.
Merit can also be seen as simply doing the right thing, and this doesn't necessarily mean doing it for all to see, but doing it to strengthen & cultivate the good, and being someone of integrity, and benefit to others, even if it is simply by cultivating the good and acting from that, that is benefiting all other beings to some extent like dominoes, or possibly more like a ripple in water, depending on the person/action.
sharing merit, as it were, isn't necessarily openly encouraging others to do likewise, or wishing for others to benefit through a dedication, but taking that wish with us in our hearts, into our lives.
Bhikkhu Pesala wrote:By giving with one's own hand, one makes merit. By urging others to give, one makes merit. If they also give, after being urged to give, they make merit. Even if they don't give, if they have the wholesome thought of rejoicing in your giving, they make merit.
Likewise for all other wholesome actions. Sharing increases the merit for both parties.
However, if those urged turn around and try to discourage, or succeed in discouraging you from doing wholesome actions. Then they make demerit, and you lose merit, or make demerit if you adopt their negative view, e.g. that giving charity, observing morality, or practising meditation is just a wasted effort.
What you write is sensible Bhante. Yet it seems that practicing virtue quietly would make it virtually impossible to encourage same. One has to either be known as a merit-making person or tell people that one is so, by encouraging them to do as I do.
Ledi Sayadaw wrote that basically indifference to the kammic results is the highest form of virtue. One is genuinely selfless and so does not even think of how, where or who one's kammas affect. But that is pretty far away from most of us worldlings. So what is wrong with aspiring to that state by thinking to oneself "May all merit from such & such acts be dedicated to all beings"? That transference will not happen, but at least it helps us get in the less self centered and eventually selfless state of mind.