That is an interesting situation. How about the next time you speak/text, to confirm the time for your next meeting, raise the topic with him: The last time we spoke, you mentioned that I overstuffed the envelope, what rate would make your more comfortable? Best way to get to a meeting of the minds, is to have clarity. If you feel he is under charging, how about you offer to do something special for him. Ask him what his favorite beverage is or if you can have wine waiting? Perhaps take him out for a meal? Send him a membership gift on Rentmen? Make a donation to Daddy or the Trevor Project in his honor? As the man said: The difference between ordinary and extraordinary is that little "extra".