I’m a first time DM with a homebrew campaign where I am hosting for my father, a long time DnD player, and his friends.
Homebrew is a bit of a challenge I will admit, but I have been able to come up with enough on the fly stuff that it’s kept it from getting totally derailed, and even the diversions are incorporated into the overall story.
My father plays a half elf rogue named Elias, the first of the two friends plays a wood elf Ranger named Hector, the second of the two plays an aasimar bard named Toke, and the son of the first friend plays a human paladin named Dave. The first friend, Hector’s player, and his son are first time players, easing into their roles.
The second friend is a long time DnD player with a bunch of experience in 5e, the rules set I am running for my campaign. And like my father, who is a bit of a trouble maker in his games which he normally Dm’s for, he enjoys having a bit of fun.
Toke’s player normally runs barbarians and other crazier classes, so branching out into bard was a first time for him. We would all soon learn how well it would fuse into the campaign.
So, as a back story for their characters, Toke and Elias know each other, and have a sort of a gig running. Toke is a bard with an unusual instrument choice: the bagpipes.
Yes. You heard it here first. A bagpipe playing bard. None of that soft flute or harp nonsense. And with some really good special magical effects thanks to Prestidigitation and a Light spell, he can make a whole room pay close attention to his bardic songs and melodies.
This is where Elias comes in. He is a really good cook by day and a gentleman thief by night, a trickster cutpurse who prefers to target the wealthy, arrogant, and selfish. His character is meant for stealth and subtlety, and it works well when paired with Toke.
The way the gig is set up, Toke distracts the audience with a headbanging performance while Elias targets a particularly snooty noble or wealthy merchant heirling being too uppity for their own good.
The result is some of the best rolling and skullduggery I have ever seen. Toke seems to always pull fantastic rolls with his bardic performance with the bagpipes, and this gives Elias a fun time snipping coin purses right off the belts of those deserving of his attentions. And every single time they make pay dirt.
Their duo is so good they can make off with hundreds of gold coins in a single night of playing in crowded inns, and it results in some of the most hilarious roleplaying I have yet seen. Session One in particular had them rob this one nobleman blind, and get him kicked out of the inn they were set up in for non-payment of his drinks. Another time, on Session Five, they made off like successful pirates with coin and gems coming out their ears.
I encourage this sort of thing because it entertains the group, and helps break up the truly monotonous moments in town, and I even have Elias as a member of the sort of mafia style Thieves Guild as a freelance agent for his backstory, and their gig is too good for the Guild to quash. But why spoil a good thing after all?