If I'm going to (say) have Alex and Bob in a swordfight at the top of the Tower of Pisa, I have to be aware that I'll need to:
... etc.
- Get them swords
- Get them to Italy
- Get them past security with the swords
- Make them both have reason to be there at the same time, with their swords
- Have a plot-and-character-relevant reason for everyone else to be cleared out of the area, or account for them if they're not
- Have character-based reasons that would justify their willingness to engage in mortal combat
- Have character-based reasons that put them in opposition to one another in the first place
This is exactly what I saw, & what I'm doing. Yours looks much neater than mine, though!
I'm a headlight writer, but knowing where I'm going to end up doesn't mean I know everything (or want to know/plot everything) along the way. I see this novel like a trip across country on I-80: I'm planning a stop in every state along the way, but I don't know exactly what I'll find when I get there, or what'll be happening. I already know who dunnit, but I don't know how my MC will figure that out, how they'll be stopped. I have an idea of how my characters will change, but I don't think I've even met them all yet so who knows?
I don't think outlining necessarily = contrived plots & wooden characters, but never having done it before I can't tell what it'll mean for me. I think,maybe, it comes down to a writer's skill & how much editing one is willing to do. That, and personal preference.
Gee, never thought I'd want to defend outlining!