1)
Why does the Pasuk say here that Yehudah was going up to Timnah, whereas in Shoftim 14:1, it says that Shimshon went down to Timnah?
1.
Rashi (citing Sotah 10a): Timnah was situated on the slope of a hill, and one ascended to it from one side and descended to it from the other side.
2.
Sotah (10a) #2: In connection with Shimshon, who was shamed in Timnah, 1 the Pasuk writes an expression of 'Yeridah,' whereas in connection with Yehudah, who was elevated there, 2 the Pasuk writes an expression of Aliyah.
3.
Sotah (10a) #3: There were actually two towns called Timnah, one on low ground, and the other, on high ground.