You'll need to consider what the scope of their abilities and knowledge are. Zhuge Liang is legendary but even he would probably struggle a bit if he was suddenly leading a spaceship armada in a pitched battle and didn't have time to learn what a tachyon drive is and the limitations of the lasers and so on. Not only that, but even if someone is a peerless tactician with no equal in their canon, there might be 15 guys who're also peerless tacticians with no equal who they might be up against so failure is an option.
More importantly, though, unlike real life strategy the success or failure of a given gambit isn't actually dependent on how smart the tactician is, how well devised the plan is, and how foolproof the thinking is. It's dependent on what people/the mods want to do.
Basically, what I'm saying is that you need to just shoot for a reasonably plausible level of tactical bullshit and concentrate on what people what to do. It's like two parts plausible bullshit, one part what's fun. Lots of OOC planning is important if you want your character to come up with plans which work, and they need to be fun for people, because otherwise you could end up with seemingly foolproof plans which don't actually work because no one wants to participate in them.
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More importantly, though, unlike real life strategy the success or failure of a given gambit isn't actually dependent on how smart the tactician is, how well devised the plan is, and how foolproof the thinking is. It's dependent on what people/the mods want to do.
Basically, what I'm saying is that you need to just shoot for a reasonably plausible level of tactical bullshit and concentrate on what people what to do. It's like two parts plausible bullshit, one part what's fun. Lots of OOC planning is important if you want your character to come up with plans which work, and they need to be fun for people, because otherwise you could end up with seemingly foolproof plans which don't actually work because no one wants to participate in them.