It can definitely take a while to get a good routine up for stuff like that :P
I agree with the "go nuts" strategy, it's definitely helped me over the years with writer's and artist's block.
Which incidentally, I'd love to know how you guys brainstorm, or if you use a particular method/program for this?
I use Word myself as well. I have a few documents for different stages of development, this is how I generally do it at the moment:
1) "Plot Cloud" - Random ideas for the story, in any order. Mostly bullet points of anything, plot points, new characters, character developments, backstories, personalities, world building, anything goes. Basically just getting my thoughts out of my head. I often expand the bullets with developed or even opposite ideas (exploring different options basically), justification, and questions for my future self to answer, like a to-do list ("when does character A meet character B, did they know each other already?" kinda thing)
2) "Developed Plot" - chosen and accepted ideas get moved here. I develop and expand the ideas, adding more finer details and padding the story timeline-wise, to get a beginning, middle and end of each plot point, roughly speaking. Making sure the point fits with the story and doesn't create many plot holes.
3) "Consolidated Plot" - The actual story outline, in the order it comes in the story. points are moved from developed plot and placed in the right order for the story to be written. Sometimes a point gets split up and spliced with other points, to make the join more seamless (i.e. hinting at an event before it happens etc, name dropping before the character gets introduced etc, and mentioning the event later on etc)
For coming up with interesting ideas within a story I already have, I sometimes use random word prompts to inspire new scenes or characters which I then go on to develop.
For example: "stay , low pressure , Woodcrafter , dizzy , aggressive"
Often a verb/adjective/noun combination gives interesting ideas to play with. Even if the idea once developed doesn't resemble the prompt anymore, then it's still done its job.