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Yes, if Bob puts in a deposit it adds a step internally.
I think for this to have a reasonable user-interface Alice and Bob's bitcoin clients will need to communicate in real time.
My inclination is to add JSON-RPC methods to bitcoin-qt/bitcoind to support this, and not build it into bitcoin-qt's GUI (or at least not right away). I'm imagining Armory or little "let's make a deal" 2-party-escrow-apps that... Do The Right Thing.
Random UI thoughts:
Alice could be asked "How much do you trust Bob?" and "How much do you think Bob trusts you?" If an answer is "not at all" then propose an escrow that requires a substantial deposit. If the answer is "a lot" then maybe no deposit is required. It'd be way spiffy cool if it was automagically tied into the #bitcoin-otc web of trust sytem...
(... more random thoughts: would IRC as the communication mechanism under the covers be a good or bad idea? might be a convenient way to prototype...)
I'm imagining Bob gets the details of the proposed escrow and can either agree or disagree (maybe with a message to let Alice know what he WOULD agree to).