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I never found a technical issue with the deal. The reasons given (from all detractors, left and right) weren't good. It was a withdrawal agreement, it got presented as something more. In it's final form it included the concessions Labour (sensibly) requested.
Basic political calculation would tell you no 'better' deal was likely to come after if May wasn't in charge. Despite this Remainers rolled a dice on stopping Brexit under the auspices of preventing a no-deal. I understand there were good intentions (as-well as bad) but it was naive and we are definitely worse off as a result.
The five word answer?
... Labour wouldn't pass May's deal.