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In Bava Kamma (17a) it says:

א"ר יוחנן משום ר"ש בן יוחאי מאי דכתיב (ישעיהו לב, כ) אשריכם זורעי על כל מים משלחי רגל השור והחמור כל העוסק בתורה ובגמילות חסדים זוכה לנחלת שני שבטים ... וזוכה לנחלת שני שבטים זוכה לכילה כיוסף דכתיב (בראשית מט, כב) בן פורת יוסף בנות צעדה עלי שור וזוכה לנחלת יששכר דכתיב (בראשית מט, יד) יששכר חמור גרם

Rabbi Yochanan said in the name of Rashb'i: what is the meaning of "Happy are you who plant by all water, who sends forth the feet of the ox and donkey"? That one who learns Torah and does chessed merits the portion of two tribes... He merits the portion of two tribes, as he merits the canopy like Yosef, about whom it says "Joseph is a fruitful vine... Its branches go over the wall (שוּר)". And he merits to the portion of Yissachar , about whom it says "Yissachar is a large-boned donkey"

My question is twofold:

  1. What exactly are these portions that he gets? I assume it's referring to Olam Haba, because it doesn't make much sense that one would get an actual portion of Yissachar's land in Israel. If so (or even if not), what makes this portion unique?

  2. Why do Chessed and Torah corroborate to Yosef and Yissachar, and which corroborates which? (I have a suspicion that this might have to do with the Yissachar/ Zevulun deal)

An answer to the first question would probably answer the second as well, which is why I'm asking them together

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