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Lumifer comments on A Challenge: Maps We Take For Granted - Less Wrong Discussion
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No, I still don't think so. In even more general terms you're talking about history counterfactuals and those cannot be settled. You're basically thinking of the case "but what if my opponent is really stupid and suggests stupid things" :-)
Certainly true. But I could probably be a very valuable adviser :-) The reason is that if I were to know military history well enough, I would know what works and what doesn't without the cost of the trial-and-error discovery.
Take a bit more ancient example: the Greek phalanx. It was considered to be an excellent formation for quite a long time, and yet the way to beat it turned out to be trivial: use highly mobile light slingers to harass the unwieldy phalanx until it falls apart. If you happen to know that, you could be a very helpful adviser to a Greek (or Persian :-D) general a century or two earlier.
Knowing how the strategy and tactics evolved in the "future", which paths failed and which did not is highly valuable knowledge.
Peltasts were commonplace in Greek warfare; they didn't displace the phalanx, or prove the phalanx's weakness, they supported the phalanx formations. This is the issue; war is considerably more complex than a "Formation X beats formation Y" equation. Roman legions continued using variants of phalanx formations centuries after the Greek and Persian war.
That said, there is technology that could be brought back to revolutionize warfare: Logistics. Modern statistical methodologies would be an incredible asset. But being the guy calculating how much food to bring and when to send deliveries isn't as exciting.
This seems like a Catch-22 situation. The original point was how to build your reputation at the beginning. Even if we assume you had some brilliant strategic ideas (which I still doubt, but let's assume you had), how would you convince them to let you, a random stranger, become their advisor?
You will need to be trusted to be allowed to lead their army, but you intended to achieve a brilliant victory to become trusted.
No, it wasn't. The OP specified (see point (3)) that you could have all the resources you need just for asking.