I usually quick save before speaking to the Captian for training and check the castle and the mages tower, if I find a relative 50 fight item (after 50 fights they give 10 runes of a colour) I take the game. The warrior and mage items are great, the paladin not so much (used to be great in TL grumble, grumble)
To answer the op question about early island fights yes! If you do find one of these items they give their runes after 50 battles, suspiciously the same number of no loss fights you need to win for grand strategy so after a island grand tour of looting and pillaging you can easily do the first two maybe three islands, that puts you very close to 50 fights, just a couple on Rusty and you should be rocking.
The only time I would really care about save scanning (it's too time consuming for my taste) is if I found a good set early on and wanted to see if I could complete it or if I found a race specific item , like the -20% leadership for red dragons, you kind of need a good and early supply of RDs :p Or maybe if I was going for the trap medal and wanted to make sure there were Archmages available in the first few islands.
But as Zechnophobe was saying it's kinda hard to get completely screwed, obviously the harder difficulty you play the more careful you would have to be with your choices.
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