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...and on your other point, of course bets should be settled correctly but I don't really have a lot of sympathy with people who bet without knowing the full rules and basic maths that apply to their bets, whether that be dead-heat rules, application of Rule 4, or other things like tennis matches that don't run the full course, especially if they are betting to meaningful stakes of the type you mention
I think that's harsh. It's easy for us "shrewdies" to live in a bubble where everyone understands odds & mathematics. Any brief conversation with your average punter will tell you otherwise.
Basic errors and typos happen but this incident sounds more a case of sheer widespread incompetence at Ladbrokes. Not only was he offered the wrong winnings but was then repeatedly told it was correct when he challenged them. I don't think you can expect most punters to be as persistent as Tom was. An utter shambles. Glad you got it resolved anyway Tom.