Answering this question, in any degree, would be largely subjective based on your definition of "more pleasant." There were certainly differences in circumstance that led to a contrast in experiences for Iberia compared to the rest of Western Europe. While some people might certainly enjoy the Spanish climate today, depending on the exact dating metric you want to use, there are many historians and scientists who would set the beginning of the Little Ice Age at 1300. The climate of the middle ages was not identical to the climate as it is today. In many places, it was often colder, with crop failure and famine. While the comparable degree of the effects of the Little Ice Age on any specific area are still debated, the 14th century and beyond certainly felt its effects and suffered accordingly, Castile and Aragon included.

Up until the end of the Reconquista in 1492, the borders of Iberia were constantly in flux as the Christian kingdoms and Muslim states struggled for supremacy. During the entire listed period, 1300-1450, wars were waged across Iberia, costing lives and resources. It was not necessarily more peaceful than many other European kingdoms. However, during the centuries before the Bubonic Plague, economic growth in Castile and Aragon was equivalent to that growth in other Western European nations. This growth slowed during the Plague, and would eventually pick up again at the conclusion of the Plague, in the later parts of the 15th century (after 1450).

Finally, and perhaps most importantly, there is a significant difference in experience based on who it is that we are discussing. Women experienced life differently than men, Catholics differently than agnostics, etc. During the Bubonic Plague, the Jewish population of Europe was heavily scapegoated as a potential cause. Any given person had their own experiences with medieval life, even among the peasantry, which included a diverse range of people. However, the life of a peasant was still full of work and survival. Huge numbers of people across Europe died during this period due to disease, famine, and war. Castile and Aragon were not exempt from this - millions of people died to these causes in Iberia alone in the 14th and 15th centuries. Barcelona was one of the major ports of entry for the Black Death!

Overall, it is difficult to qualify the human experience in such definitive terms as "easier" or "harder", but the Iberian experience was certainly a difficult one. It didn't escape war, famine, or disease, and suffered through them just as much as the rest of Western Europe did. Castile's economy would begin to grow drastically shortly after the 1450 cutoff, and would surpass that of many contemporary states, but not until later after the described period.

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Bibliography:

Climatic Change and Witch-hunting: the Impact of the Little Ice Age on Mentalities by Wolfgang Behringer

Economic Life in Late Medieval and Early Modern Spain, 1085-1815 in the Oxford Research Encyclopedias by Hilario Casado Alonso and Teofilo F. Ruiz

Was The Little Ice Age Triggered By Massive Volcanic Eruptions? by the National Center for Atmospheric Research & University Corporation for Atmospheric Research (published January 30th, 2012)