D&D 4E Converting a 4e skill challenge to 5e: looking for suggestions...

[Remathilis]

Rather than giving your players a menu of tasks to choose from, I would set out the scenario and give them the intel I wanted them to have on the approaching enemy, then simply ask each of them what they want to do and how long they plan to spend doing it. Maybe suggest half-day or full-day efforts. Let them come up with the ideas.

The leader of the Rebellion will suggest a few things (aka the list) if they don't know where to start. They are free to come up with others if they want. The idea was that they'd get one important thing done a day; along with minor things, etc.

This isn't supposed to be a big part of the adventure; the battle upcoming will be much bigger. Its more to give them a feel of preparing and have that feel reflect in the later combat without getting into the nitty-gritty of actual tactics and stuff. Even moreso, what I posted was my DM notes; a lot of these events will be given some "meat" via role-playing and description much like how a combat can be given vivid description rather than be reduced to a series of dice rolls and number calls.

 

[iserith]

If you have 5 players at your table and are effectively going around the table a maximum of three times, I predict that by the second go around, players will really be struggling to come up with things to do even with your list. For this and other reasons, I recommend flipping it around and present complications to be resolved rather than leave it totally open to the players to suggest things to do proactively (or for an NPC to do that).

For example, I would present the complication of Frayed Nerves. "As you circulate among the troops, there is a palpable tension. Nobody has ever defeated Lord Badguy's army in the field - nobody. Fear is a cancer and it is spreading through the ranks. What do you do?" A solution might then be to "entertain the troops" and you can adjudicate it with success, failure, or an ability check based on the player's stated goal and approach for the character. Then I'd present other complications like Green Officers, Religious Doubt, etc.

This provides the players with something to grab onto when it comes to figuring out what to do next.

 

[Manbearcat]

If you have 5 players at your table and are effectively going around the table a maximum of three times, I predict that by the second go around, players will really be struggling to come up with things to do even with your list. For this and other reasons, I recommend flipping it around and present complications to be resolved rather than leave it totally open to the players to suggest things to do proactively (or for an NPC to do that).

For example, I would present the complication of Frayed Nerves. "As you circulate among the troops, there is a palpable tension. Nobody has ever defeated Lord Badguy's army in the field - nobody. Fear is a cancer and it is spreading through the ranks. What do you do?" A solution might then be to "entertain the troops" and you can adjudicate it with success, failure, or an ability check based on the player's stated goal and approach for the character. Then I'd present other complications like Green Officers, Religious Doubt, etc.

This provides the players with something to grab onto when it comes to figuring out what to do next.

Good post isereth. This is the route I'd go if I was running 5e. I'd treat this situation sort of as a "poor man's DW." Frame each PC (or the PCs as a group) into a conflict such as the ones mentioned above or something like Bloody Coup, Dissension in the Ranks, Deserters Stole the Horses (etc).

Come up with 5 or so "Fronts" that have to be dealt with. Use the DMG variant of fail by 1 or 2 and the PCs can choose to mitigate the immediate failure, turning it into a success but the situation snowballs/evolves with further danger (introduced by the GM) that the players have to deal with. A failure by 5 or more cements a failure in that "Front" and the PCs have to deal with the fallout. Success by 5 or more cements a success on that "Front" and the PCs accrue assets/relationships for future conflicts.

I would definitely not just give the PCs a broad "here is a bunch of stuff - GO" approach. Make them be proactive in a micro-situation with some tight zoom. They'll surprise you, be mentally engaged, and do cool, thematic stuff. Zoom too far out and they may just feebly meander about, accidentally create more trouble than the resolve, or bring what should be a rigorous pace to a grinding halt, simply because lack of focused cues/stuff in their face lends them toward being unsure about what adventure/danger is engaging them.

 

[Remathilis]

If you have 5 players at your table and are effectively going around the table a maximum of three times, I predict that by the second go around, players will really be struggling to come up with things to do even with your list. For this and other reasons, I recommend flipping it around and present complications to be resolved rather than leave it totally open to the players to suggest things to do proactively (or for an NPC to do that).

For example, I would present the complication of Frayed Nerves. "As you circulate among the troops, there is a palpable tension. Nobody has ever defeated Lord Badguy's army in the field - nobody. Fear is a cancer and it is spreading through the ranks. What do you do?" A solution might then be to "entertain the troops" and you can adjudicate it with success, failure, or an ability check based on the player's stated goal and approach for the character. Then I'd present other complications like Green Officers, Religious Doubt, etc.

This provides the players with something to grab onto when it comes to figuring out what to do next.

I assumed that a few PCs will try to double up on some actions, thus the repeated success limit.

As for the "in game", what you are describing IS how the fiction is going to handle it. "We need help drawing up battle plans" or "there is dissent among the ranks, any ideas how to fix it?" while also allowing the PCs to choose other actions. (Or no action, if they want to Achilles this event). Multiple uses can cover either repeated tries or continued effort.

That said, 3 passes MIGHT be too much; perhaps 2 passes with adjusted successes (6-8? I've shooting for 1/2-3/4 success ratio; but that can be tweaked.) My main goal is that many of these events can be handled with a single die roll and some RP; drawing out each complication is going to steal away time from the major concern which is the massive set-piece battle happening during the "war".

Though all of this has given me more focus on how to move around "during" the event. Thanks.