This is a reference to an Avalon Hill game I played decades ago as "Rommel." My opponent, "Chuck" was one of the best players in our group, I was considered above average, but an underdog compared to Chuck. (This evaluation applied to chess, monopoly and other games, not just AK.)
Playing England, Chuck left a token force in Tobruk, and dared me (Rommel) to capture it. I did so in June, 1941 (basically the first opportunity), using my whole force. He then besieged me in Tobruk, counting on the mountains to double the defense value of his forces. I had two turns to roll for resupply. I would fail only if I rolled a one or two (on a six sided die) BOTH times, one chance in nine. I failed, lost the Afrika Korps, and the game. We had discussed the possible outcomes during the dare so I went in with eyes wide open.
Do you like those (presumed) 8 to 1 odds for Rommel? Did Chuck know what he was doing when he made the dare? Even if this is the case, was my strategy a reasonable do or die strategy that gave me the best chance to win against a better player?
I would give the most weight to answers from people who have actually played the game, but would consider answers based on real life. E.g. "Tobruk was such a major objective historically that it's worth staking everything on it, if the game mirrors real life." Or, "you needed to do something before England receives reinforcements in November."
More tidbits about the game. 1) The British have more combat factors overall. 2) The Germans have more combat factors until November, 1941 when the British receive heavy reinforcements. 3) The Germans have fewer, but more powerful units (e.g. tank divisions with a value of 7, versus a maximum of 4 for British armor, and 3 for British infantry. 4) The British have "automatic" supply, the Germans have to roll for supplies.