Sorry that took forever! I had difficulty figuring out how much control I had with the other team. Had I come here first, I think I could have solved a lot of my problems. -_-
Apologies also if my post was in some way inconsistent with those before it. Again, if I had read Digi's chronology here first it would've been an easier write.
As for your questions, Digi,
How can I as a Game Master better explain or make up tactics that Oliver creates? Perhaps we just need to dedicate more time to the pre-game strategy. A single paragraph embedded in the middle of a long post is not very easy to respond to. But if its closer to the end, then characters who are more independent will have time to voice objections. Maybe?
How can I as a writer make the plans more understandable? For me, it was difficult to understand only because so much was going on in the same paragraph. When Oliver describes what he believes is the Storm Chaser's strategy, he simultaneously describes how his team should counteract it. Rather than discuss both at the same time, I'd suggest leaving the other team's strategy out. Let Oliver direct his team as he sees fit. Consider writing out what Oliver is thinking only if another character asks. After all, introspection is not something a roleplayer can respond to.
How can Oliver make strategies while making best use of your characters skills and personalities? Maybe this warrants further planning. Perhaps our characters' personal tactics, battle strategies, strengths, and weaknesses should be something we add to our bios.
How can Oliver make a plan that the other characters would want to follow? Since the canon of this world is that Oliver is a respectable leader with incredible intuition, there is no reason our characters shouldn't follow him. I'm content with how he leads now.
How can I make tactics that leave plenty of room for creativity from you guys? I think what you did earlier was perfect - give vague enough orders that allow the players to decide how they want to carry them out. I think the confusion with Fandrim and Elizabeth "going rogue" just boils down to miscommunication.
I hope this helps, but please take it with a grain of salt. :)