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The Tanya said food eaten on Shabbos is automatically elevated. I hear from a chossid that people should not do hiskafia on shabbos. However, the local Rosh Yeshiva said that eating more is not a mitzvah on Shabbos, that a person should eat normally. I find that the amount of food eaten is always in inverse proportion to the amount of Torah and productive work I am able to accomplish.

There also appears to be injunctions to eat more on Chol Hamoed with the caveat that we shouldn't neglect the ruchnius either. Is there a mitzvah on Chol Hamoed to eat beyond the two seudahs per day? If so, how much? Is it as much as pleasurable?

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The laws of eating meals on Shabbat are well-known and don't appear to be the core of your question, in any case Kitzur Shulchan Aruch (KSA) 77:16 provides a good overview.

The same KSA in siman 103 provides a number of relevant rules regarding meals on Yom Tov. I picked a number of them but it is good to read the original.

Just as it is a mitzvah to honor the Shabbos and delight in it, so it is a mitzvah to honor all the Yomim Tovim [...]

What is meant by delight? [...] on each Yom Tov day you must have two meals, one at night and one during the day, but it is not our custom to have a third meal. [...] you should be lavish with meat, wine and sweets, according to your means.

Every man is obligated to gladden the hearts of his wife, his children, and all who are dependent on him, in a way suitable for each [...] to the men, meat and wine. It is the custom to serve a greater variety of foods on Yom Tov than on Shabbos, because with regard to Yom Tov, the Torah mentions "rejoicing," but it is not mentioned with regard to Shabbos.

Even though eating and drinking on festivals is a positive commandment, you should not spend all day eating and drinking [...]

And when you eat and drink, it is your duty to provide also for the orphan, the widow and other needy people [...]

When a person eats and drinks, and rejoices on the festival, he should not overindulge in drinking wine, in laughter and lightheadedness, thinking that the more he indulges, the greater will be the mitzvah of rejoicing.

KSA doesn't explicitly address meals on Chol Hamoed. R Aharon E. Marcus, in his excellent Halacha 24/7/12, writes (p. 264)

According to most Poskim, you should have a reviit or wine and a kezayit of meat every single day of Yom Tov, including Chol Hamoed. R Shlomo Zalman Auerbach says that grape juice and poultry qualify as meat and wine, but R Moshe Feinstein and R Eliashiv say that you should consume alcoholic wine and beef.

Similarly R Dovid Zucker and R Moshe Francis in their book on the laws of Chol Hamoed p. 21 write

[...] each person should rejoice in the manner most compatible with his nature. Thus [on Chol Hamoed] according to many authorities, a man should drink a reviis of wine daily (some authorities allow grape juice instead of wine). It is also preferable to eat a kzayis of meat daily [and it is even permitted for women on their mikve day] (see there and appendix for sources)

See also here for the views of Shulchan Aruch HaRav.

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