Anyway, the contexts are about tactics to solve a problem in front of us, like in a battle. We're pretty good at that. That's our strength.
First:
As
@eaglejarl pointed out, pretty much any general class of ideas ("We should acquire apprentices!" "We should do a heist." "We should start a business." ) contains enough variations that it could practically be applied to advance pretty much any sort of goal in some way.
It is downright baffling to me that such things are often met with "Hello what about obvious problem? This does not account for this. Bad idea."
Often to me, this devolves into sniping over trivial low hanging fruit. I become mildly skeptical that the other individual has actually put any due dilligence into the conversation besides throwing the first reasonable objection that came to mind because it boils down to "This is a thing I don't want to do."
A simple "I don't want to do that." with no continued justifications would suffice there, though of course "I don't want to do that, but would you exchange voting for this idea I have in return if I support a reasonable implementation of yours in kind?" is much better.
It baffles me how often people declare entire classes of ideas to be garbage by fiat, without pursuing any of the other options above or seemingly examining them.
Second:
One of our main issues at the moment is lack of mid-term planning. We do not actively set up tactical elements for future plots. Even those that we have not thought up yet.
We are, consistently, the kid that rushes to do their homework ten minutes before handing it in, instead of the one that already has half the book of exercises typed up before they're even assigned. Obviously the latter is an unreasonable goal to reach for, but being content with the other side of the scale is equally bad.
Even a purely hypothetical heist plot would be a fantastic exercise. Theres so much we would have to actively get sorted out in advance that it would be really good practice in plotting things over a period of time.
(Aside: we should be put in charge of Leaf's chunin exam events next time we host. This would be a fun event to design.)