Assuming both have 5 pips left to bear off, if red gets on roll he always wins (white drops the offered 8-cube). So red wins if white rolls any 1 and loses to everything else, so if he takes the cube he loses 4 25/36 and wins 4 11/36, for an equity of -1.56 points. If he drops he loses 2 100% of the time for -2. So taking is correct by a good bit here.
White doesn't bear off both checkers if and only if he rolls an ace, so he has 25/36 odds to win immediately. If he misses, red redoubles and it is pass (more than 27/36 winning rolls for red in that case)