From the Gemara in Pesochim (3b) it’s clear that R’ Yehudah ben Beseira never went to Yerusholayaim to bring a korban pesach. In explaining why he never went, the Tzlach says a big chiddush [novel ruling] and explains that the reason R’ Yehudah ben Beseira never went to Yerusholayim to bring a korban Pesach, was because he lived far away, and we don’t find that one is obligated to start being oleh regel [going up to Yerusholayim] before the time of the obligation to bring a korban pesach, and when the 14th of Nissan, the time to bring the korban pesach arrived, he was “bederech rechokah” [to far away].
However, the Minchas Chinuch (Parshas Bo, Mitzvah 5, s.k. 13) argues and says: “Certainly there is a mitzvas aseh [positive mitzvah] upon everyone in Klal Yisroel to bring a korban pesach like every other mitzvas aseh, and one must travel from the other end of the world to get closer and be able to do the mitzvah. If we don’t say this, everyone in Klal Yisroel, even those living in Eretz Yisroel who are more than fifteen mil away from Yerusholayim will be exempt from bringing a korban pesach. It will then come out, the majority of Klal Yisroel will be exempt from Pesach Rishon, and they won’t bring a korban pesach on Pesach Sheini either, as the majority of Klal Yisroel can’t bring a korban pesach sheini (Pesach Sheini is only for individuals).”
The Ohr Some’ach (Hilchos Korban Pesach 1:18) also takes on like the Minchas Chinuch that one must prepare for bringing the korban pesach before the 14th of Nissan. However, all his proofs are in regard to korban pesach, and we can’t prove anything from here in regard to other mitzvos.
The Lekech Tov (R’ Yosef Engel, Klal 6, s.k. 3) speaks about this question at great length, and brings various proofs from fourteen different places in Shas, if when it comes to mitzvos which apply at certain times, if one is obligated to worry about the mitzvah before the time of the mitzvah or not. I.e. Does the mitzvah of succah and lulav start only on Succos and one doesn’t need to be worried about it beforehand, or do we say there is an obligation incumbent on one even before the time of the mitzvah to do what he can to ensure he can carry out the mitzvah when the time for the mitzvah arrives, and he must prepare for the mitzvah beforehand.
We see there is a machlokes haposkim if one is obligated to do things before the time of the mitzvah to ensure he can do the mitzvah, i.e. is one obligated to start travelling to Yerusholayim before the 14th of Nissan so that he is close to the Beis HaMikdosh on erev Pesach, or not. Therefore, in our case as well, it would seem there is a machlokes if it is fitting for the bochur to do what he can to ensure that he can daven with a minyan on Yom Tov Sheini. According to the Tzlach there would be no need to do anything, and according to the Minchas Chinuch he should do what he can before Yom Tov to ensure that he has a minyan for Yom Tov Sheini.
However, there is a big difference between the case of korban pesach and our case. By korban pesach, the only place for the mitzvah is Yerusholayim, therefore, the Minchas Chinuch holds, since there is no way in the world to fulfill the mitzvah except by traveling to Yerusholayim, traveling to Yerusholayim before the time of the obligation is part and parcel of the mitzvah and one is obligated to do it. However, in our case, davening with a minyan on Yom Tov Sheini with Bnei Chutz La’aretz doesn’t necessarily require one to travel to another city, therefore, we can’t say that traveling to another city is part and parcel of the mitzvah of davening with a tzibbur. Therefore, our question remains, if it is fitting for the bochur to travel to another city so he can daven with a minyan and hear krias haTorah on Yom Tov Sheini, or if it is perfectly ok for him to stay in Yeshivah?