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When is a model category with a compatible -enrichment , has tensors and is the walking isomorphism, will be a cylinder object of ? I can factor the fold map as , but I don't know how to check the other conditions.
Yes provided that is cofibrant and "compatible Cat-enrichment" is interpreted suitably (as in https://ncatlab.org/nlab/show/enriched+model+category, for a suitable model category structure on Cat).
To check the conditions to be a cylinder object, apply the pushout product axiom to: (a) the cofibration of and (b1) the acyclic cofibration of Cat, (b2) the cofibration of Cat.