Excuse the pun, but it seems to me it was an accident waiting to happen somewhere along the way.
My impression is that most owners of such exotics (Piper being an apparent exception) understand that in owning such cars they should be driven, rather than festering in a private mausoleum. Classic racing is a common route and experienced drivers (which Hales is irrespective of being a motoring journalist) are entrusted to take the wheel on not much more than their reputation and a Gentleman's handshake. It's implicit that should the car break, the owner picks up the tab. It's regarded as "going with the territory". Racing these cars and allowing them to be tracked for magazine pieces does also enhance the cars pedigree, so there is a financial incentive for the owner also. It scratches both itches and I'm sure it will continue to in the vast majority of cases - Goodwood, Classic Le Mans, etc, etc.
From what I can tell this was not the case here however, but rather a similarly vague "you bend it, you mend it" agreement. If this was indeed the case then Hales was a muppet for not fully clarifying the terms. Comments posted on PH referring the the court transcripts seem to show a very muddled agreement as to what Hales should or shouldn't have done whist behind the wheel, particularly important given the car in question is renowned for lunching it's engine.
I have to say my sympathies do lie with Hales, with Piper coming across as someone only looking to improve the value of an asset before shifting it on, whilst in the meantime covering his @rse should any failures occur, but if the agreement was based around "you bend it, you mend it", Hales should have put adequate cover in place or walked away.
I hope the fund being put in place takes the burden off Hales, and perhaps this case will at least serve to clarify those occasions where a Gentleman's agreement is not enough.