What were the political and military constraints on Vercingetorix at Alesia?
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Although I read War of the Gauls a long time ago, my answer is based on a fairly recent listen to Dan Carlin's Celtic Holocaust podcast.
Now, Carlin's not a real historian, but comes a damn sight closer than most of us and in any case is just going to be doing the same thing as everyone else: looking at Caesar's book. Which, for all its lack of corroboration and self-serving propaganda, is a damn sight more documentation than a lot of ancient history gets.
Leading up to Alesia, the basic facts (and claims) are as follows:
by the time of V's revolt, Caesar had been campaigning in Gaul for a while and had largely subjugated the individual tribes.
Gaul was not a unified country, and Caesar had not been fighting a king or kingdom. Rather, he had been taking out tribes one by one or in small groups.
V is chosen/elected as a unified war leader, but still answers to tribal politics. His central authority is unprecedented, for the Gauls.
V explicitly recognizes the superiority Romans enjoy in set piece battles and wants to target their logistics. Essentially, he wants to fight a large scale guerrilla war, using scorched earth tactics. But he doesn't have say Stalin's authority to just burn things. He does it, but it's not popular. Neither, probably, is "cowardice" to the Gauls.
Alesia (according to Carlin):
Is supposed to be extremely well-fortified and is supposed to have political/cultural significance. A "town worth fighting for". V finds it difficult to convince his confederacy to just burn and leave.
Roman superiority in set battles and in sieges was well known, but the Gauls might have not fully appreciated how capable they were. Think Masada or the crossing of the Rhine - double-walling Alesia looks extraordinary to us already, let alone folk without our hindsight or other Roman examples to look at. They may have thought they could hold out.
The numbers on the Gaulish side are immense, maybe even too large to be credible. But keeping large armies in the field has always been a weakness tribal systems have when fighting established imperial powers. It could be that the Gauls felt they had sufficiently hurt Caesar and needed to force an outcome.
As V. was not a king but rather an elected/chosen war leader, he might have limited leeway to cut and run and fight another day. By running away, either before he got pinned, or later on, he might have lost his claim to leadership. That would really depend on the power and influence of the tribe that owned Alesia.
Evacuating the civilians is also easier said than done. I am pretty sure the standard Roman response to insurrection tended to enslaving everyone. So it might have at first seemed safer to keep them in the city and wait for the relief force to fix the whole problem, rather than turning them out (from their own city) sufficiently long before the Romans arrived. V does try to send them out later, and the Romans send them back, precisely to hasten starvation.
In short, given the Gaulish numbers, his political position and the relative success they had had until then, V might just have miscalculated and bitten off more than he could handle. On the other hand, we know what happened and we know that sitting in Alesia was a death sentence, even if we don't know all that much about the bigger picture and possible alternatives. So it's natural for us to assume a clever leader would not have made this mistake.
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