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When you know you won't be able to be online for too much. For example in exams week, or if you're going on a vacation trip. The special gem boost has gone and I doubt there is going to be another anytime soon.
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At the end of TH8 I only had 1 PEKKA barracks (3 drag), I upgraded 1 more before TH9 finished, and I had 1 dark barracks upgraded to golems. At TH9 I upgraded the dark barracks to witches and that was it. Then while I was upgrading defences the lava hound was released but I had no interest in it so left it. At the end of TH9 when I didn't need the builder and when I wasn't farming as much I put 1 builder on to work on barracks. Built the second dark barracks and got them all to max.
Losing a barracks has never bothered me tho, whenever I boost its always for barch so I only boost 2 normal barracks anyway. It was always losing the builder that bothered me. That's why I wait till I don't need him.
Although once i started doing GoWiWi attacks in war, 1 dark barracks did start to annoy me lol
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Upgrade them all when it becomes available. I laugh at the people with 1 level 10 barracks and 3 level 5. How they efficiently train any army like that is beyond me.
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obviously when you go on vacation without a phone lol.
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I upgraded my last two barracks to level 10 the same time I upgraded my town hall to level 9. I had completely maxed out th8, and the last few buildings were two barracks which finished two days before my town hall.
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accumulate a ton of elixir and upgrade 3+ barracks.
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Last two buildings I upgraded as a Max TH10 were my remaining two lvl9 barracks. So yea, if you have one with pekkas for war, you're good to go. I never stopped raiding long enough to upgrade them :D