Thanks to the power of the internet, I'm rewatching a favorite: Robin of Sherwood.
So in inspiration of this, I'm asking the following:
How would you do a band of merry men in 5e (assuming the PCs are said merry men)?
What party would you build?
It depends on how high a magic level you’re willing to indulge for accuracy to the setting concept vs adapting it to DnD, rogues and rangers i think are obvious, monks(drunken master, kensei, shadows) and bards(eloquence, lore, swords) possibly some clerics(trickery, twilight, nature) or a warlock or two of the right pact(archfey, genie), a druid or fighter fit in well enough.
Edit:the focus imo is on stealthy mobile types, being tricky and smart rather than the big tanky fighter dude in noisy heavy armour, short/longbows are the iconic weapon but shortswords/knives and staffs also fit the aesthetic, maybe some handaxes, spears, throwing hammers or clubs, think about what you can reflavour to match available tools
what obstacles would you have to deal with?
I’m a little unclear who/what this is meant to be directed at specifically? Assuming you mean the players, resource management, keeping up ammo, potions and rations/fresh food and water(ban goodberry, tiny hut and the like) while trying to not get discovered by the sheriff and royal guards out for the wanted criminals, keeping themselves informed of opportunities to liberate gold for the needy or of upcoming raids by the guards meaning they need to relocate home base in the forest(itself a challenge to present them with how to do this)
What would be in the woods to help/hinder the party?
To help: Natural illusions, communicating with the animals/plants, ruins of old structures, caves and tunnels, magical creatures/fey
To hinder: also natural illusions, beasts/magical creatures/fey, dangerous plants, guard patrols and less moral bandits,
What magic would be expected to be used to turn Sherwood forest into a fortress?
As mentioned above, illusions and speak with plants/animals, commune with nature, enchantments to confuse and misdirect, control plants, plant growth, (permanent?) wall of earth/stone and stoneshape to build fortifications, awakening on the animals.
How would gameplay change when you switch tiers?
This im less certain on but probably small skirmishes in the woods/town, more focus on stealth/hit and run or escaping guards rather than defeating them>>specific missions to acquire allies or neutralise lesser threats(bandits, large wild beasts), rescue NPC prisoners+acquiring resources to improve equipment >>building a defendable home base to defend+Defending it>>raiding the castle to fight the final battles with big names enemies.