Q. It says to spend more money on matanos laevyonim than on the other mitzvos of Purim. However, if there are many people that I owe to them hakaras hatov (giving thanks for favors received), and I feel obligated to give them mishloach manos as an expression of my hakaras hatov, would doing so take precedence over giving more money to matanos laevynonim?
A. Mishna Berura (694: 3) indeed rules that it is preferable to augment and increase the gifts to the poor over the Shalach Monos givings. since there is no greater joy and exquisite simcha as bringing happiness to the needy and destitute.
However, Horav Shlomo Miller's Shlit'a opinion is that both mitzvos of Purim are most important and essential.
Since there are many variables and changing factors on each case, it requires common sense to establish the correct equilibrium between these two basic obligations.
Rabbi A. Bartfeld as advised by Horav Shlomo Miller and Horav Aharon Miller Shlit'a