What are the connotations of "va'Teishvu be'Kadeish"?
Rashi (in Iyov, 22:8): It means either 'You were held-back' or 'You spent a long time'.
Targum Onkelos and Targum Yonasan: It means simply 'You dwelt''.
What are the implications of the term "Yamim Rabim" both here and in 2.1?
Oznayim la'Torah (in 2:1): It implies a. literally a long time and b. bad times. 1
And by the same token, good times seem to be short - as in Vayeitzei Bereishis, 29:20.
What is the meaning of "ka'Yamim asher Yeshavtem"?
Rashi (citing Seider Olam): It means that they remained in Kadesh as long as all the other travels put together. They spent thirty-eight years in total in the Midbar after the Meraglim, 1 nineteen years they spent in Kadesh and nineteen years traveling, 2 at which point they returned to Kadesh. 3
Rashbam: And Yisrael knew how many years were involved. 4
See Sifsei Chachamim.
See Oznayim la'Torah, who, citing the Seider Olam, actually inverts the order and elaborates.
To teach us the Chesed of Hashem, who gave them respite for such a long period even after the harsh decree. See Oznayim la'Torah.
See Oznayim la'Torah who cites the Ibn Ezra's explanation and queries both explanations.