Which (hēn). Agreeing with skēnēn, not with tupon.
In their turn (diadexamenoi). First aorist middle participle of diadechomai, to receive through another, to receive in sucession or in turn. Late Greek, only here in N.T. Deissmann (Bible Studies, p. 115) argues from a second century b.c. papyrus that diadochos means rather deputy or court official than successor.
With Joshua (meta Iēsou). With Jesus, the Greek form of Joshua (contracted from Jehoshua, Mat 1:21), as in Heb 4:8.
When they entered on the possession of the nations (en tēi kataschesei tōn ethnōn). Literally “in (or at the time of) the possession of the nations.” See note on Heb 7:5 for the only other N.T. instance of kataschesis.
Which (hn). The nations, genitive by attraction to case of ethnōn.
Thrust out (exōsen). First aorist active indicative of exōtheō, to push out, common verb, here, only in N.T. save some MSS. in Act 27:39.