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Good points, and these are stumbling blocks that the Semantic Web will need to overcome - and I'm sure it will in some respects.
The W3C are putting effort into the Trust issue, which may involve XML Signatures, and perhaps Google-style 'trust through relationships' ranking of organisations (there's some interesting thoughts at http://www.w3.org/2002/03/key-free-trust.html).
This issue is valid even today; even if you buy your tickets first-hand, you may not know if the supplier will deliver. I suppose we trust our judgements through brand recognition; perhaps the agent could be pre-configured with a set of authorised agents (only compare and make purchases from these 20 sites, or those that can provide a valid SSL certificate)?
The leg-room issue is a tricky one; though if the sites used Theatre-Seat Mark-up Language (TSML), the agent wouldn't have a problem...
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