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Leo's guess is actually right. For reference, it is enough to go on the wikipedia page of お負け. The meaning originally comes indeed from the fact that the seller is losing something in the bargaining process (from wiki): おまけの語源は「御負け」の文字通り、店員が客との駆け引きに負けて値を下げる行為を指す言葉であったが、のちに商品以外の物品を追加する行為なども言うようになった.
I feel this topic-introductory use of 「だったが」 is licensed by the relative clause 「12世紀後半、父への反発心から獅子心王リチャード率いる十字軍遠征に参加した」 modifying the topic word(s) 「(英国貴族ロックスリー卿の息子の)ロビン」. Here, what is being introduced is not merely a person, 「ロビン」, which in itself lacks specific temporal reference, but a person and his action in the past (or "the past of the past"), ...
I can't think of any straightforward uses for お負け as "exaggeration", but it could be used like this: 彼の話にはいつもなんらかのお負けが付いている "There's always a little something more to his stories" This might imply an exaggeration... Sidenote: おまけ can also mean menstrual cycle
Although, I think I do understand the meaning of it In one hour before 8:30 am, when the reservations started No, this sentence means "By 8:30 AM, which is an hour before the registration started, ...". The actual registration starts at 9:30, which is written at the end of the article. Here, の is used as the apposition marker. 友達の田中さん ...
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