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The conclusion I ended up coming to was that because of how weak the mounted archer is in Early Middle Ages (it has lower attack than an Iron Age archer as a trade off for its mobility) perhaps an all armoured infantry set-up would be able to roll through the whole thing without even needing any rogues and at a reasonable level of boost. Ideally I also wanted to avoid too much dependence on rogues as they can be difficult to obtain in large quantities without an Alcatraz and an Alcatraz is a serious extra investment. I had one server where I was in contemporary age and found that to be an exceedingly simple age to clear quickly, but obviously getting a server to contemporary age to begin with is a lot of work! In general, an Alcatraz, Zeus, Cathedral of Aachen, and Castel del Monte would make most any age doable, but these are all buildings that need serious levelling work to be effective.
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Still, the question I was most interested in at the time is what age(s) were ideal for setting up to run all 3 difficulties of expedition with the least amount of work. Running expeditions for diamonds is a little more work intensive but doesn't take quite so many events to get the ball rolling. Between events you log into the world once a day and collect your wishing wells which have a roughly 1% chance each of giving you 50 diamonds. Traditionally the optimum strategy for doing so has been to participate in events to get diamonds from quests and to place wishing wells. Diamonds are the only thing that crosses between worlds on your account (note that beta and other regions are separate accounts and thus do not share diamonds). Diamond mining is play alt-worlds to win diamonds to use in your main one. One of the things some of us have taken on since the advent of guild expedition is running it on many servers for the purposes of diamond mining.
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