> Calculating the risk which is involved in the event of failure, he demanded a show-down with the other party.
This doesn't sound quite right to me (tense mismatch, awkward wording). Would the Japanese match something like "After calculating the risk of failure, he demanded a showdown with the other party"?
しながら = While
While keeping the risk in mind / While taking the risk into consideration = After calculating the risk
I think it’s probably OK but I’d probably wait for CK or tsp_2, they have better knowledge of both these languages than I do so can make better advice
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