The breach of contract committed by Jesse is clear. The focus is on what losses are recoverable. On the traditional approach to remoteness under Hadley v Baxendale (1854) 9 Exch 341 the towage and repair costs seem to fall under Limb 1, whilst the missed flight falls under Limb 2. The latter is difficult: Jesse did know of the flight at the time the contract was made, but is this sufficient for Jesse to recover such losses? This important issue must be considered, and reference to The Achilleas  UKHL 48,  1 AC 61 and the concept of ‘assumption of responsibility’ should be made.
That is the major aspect of this question. But other issues deserve attention. For instance, is this the type of contract for which Jesse can recover for mental distress (cf Farley v Skinner  UKHL 49,  2 AC 732)? Is it possible to recover for Flynn’s loss (cf Panatown, and see too Chapter 10)? Is it possible to recover for the supposed loss of a chance here (cf Chaplin v Hicks  2 KB 786)?