If you have a bard in your party and want to get more mileage out of the Performance skill, I present to you my rules for busking in 5e (though it could pretty easily be adapted to any other system).
Players can choose to busk as a downtime activity if they are in a civilized area. If the players are busking in game time, wing it with the time they spend busking.
Roll Performance (if performing as a group, roll with advantage in 5e). Multiply the roll by # of days spent busking. The busker receives that number in
- Coppers or equivalent if busking in a village (street), or a disreputable part of town.
- Silvers or equivalent if busking in a city (street)
- Electrum or equivalent if busking in the cultural sector of a city or a city renowned for the arts, or the inn of a city, or a public amphitheatre in a city.
Now the fun part. Roll on the Random Busking Encounters table below. I suggest directly RPing this whether you're busking in downtime or game time.
The Performance check determines how to roll on the table:
A Nat 1, roll with disadvantage.
A roll between 1-9, roll a d6A roll between 10-15 roll a d12
A roll of 15+ roll a d20
A Nat 20 or any roll in excess of 25, roll with advantage.
RANDOM BUSKING ENCOUNTERS
1. Scandal: You said, did, or performed something offensive to the local populace during your set. Receive no gold and you are no longer able to find employment as a performer in this city until such time as public favour returns your way.
2. Play Wonderwall: You've attracted an unfortunate hanger-on, a heckler, an obsessive fan, or
someone else equally unpleasant who drives the crowd away. Halve money earned.
3. Trespassing: You've inadvertently begun performing in an already staked area. Maybe a bard's alliance lays claim and requires a membership fee, the city bylaws require a busking permit, or a thieves' guild wants a tax for being on their turf. Whatever the group is, they will ask for d% of all busking profits in that area. The PCs can refuse but must deal with the repercussions.
4. Murphy's Law: Something unpleasant and unexpected happened. Roll on your Random Urban Encounters table, or if you're feeling gonzo, a Wandering Monsters table. Strange rumours circulate about you in response to this incident.
5. Technical difficulties: Something you use in your performance (instrument, costume, script, etc.) is stolen, destroyed, or damaged. You'll need to find a way to get it repaired or fixed, or develop a new act.
6. Harsh words: Someone has it out for you. Your performance was poorly received by a local critic, a patron of the arts, a nobleman, etc. They disparage you openly and publicly. Roll with disadvantage when busking in this area unless you manage to rehabilitate your reputation.
7. Afterparty: Carouse!
8. Dark materials: You made no money. Where was the crowd? It seems unseasonably overcast. And what was the deal with that one guy who left you: 1-3 something entirely useless, a shoestring, a cork, a frayed playing card, 4 a trinket, 5 a strange idol, 6 a random magical item (would suggest something consumable), probably cursed or, if a consumable, likely to have unintended effects (see here, here, or here)
9-12. Business as usual: Nothing particularly interesting happens.
13. Damn fine performance: You're in the zone. d% extra currency earned.
14. All abuzz: Something was especially remarkable about the performance, or someone important has taken to you. Word of mouth spreads quickly. People will be talking about you. Roll with advantage the next time you busk in this area.
15. Imitation is the sincerest form of flattery: You're a trendsetter. Your style is taking off locally: being codified into a genre, trend, etc. Imitators abound. You're even more well known than before, but consequently, you're at the risk of becoming passe if you don't change up something in your act or dissuade your imitators.
16. New friends: Your performance attracts: 1-3 a new hireling, contact, or friend, 4-5, a random animal companion (dog, goat, badger, snake, bear, psuedodragon, etc.) who joins your act, 6 a familiar
17. Interested eyes: Someone important has noticed you. You have: 1-2 been invited to play at the manor of a wealthy patron of the arts, 3-4 been invited to play a large show(s), 5-6 been offered a publishing deal (or equivalent based on genre & time period).
18. An instant classic: That'll go down in history. New-found fame attracts attention, both wanted and unwanted.
19. Keep it secret, keep it safe: While sorting through your tips, you find something you hadn't noticed: 1, a magic rope, 2 a magic candle, 3 a potion (as normal, or here and here), 4 a spell scroll, 5, something from someone you haven't seen in a long time, 6, a random magic item.
20. Lightning in a bottle: You'll never have a performance like that again. Roll twice on the table. Double currency earned after all encounters are resolved (in order of low to high).
This'll keep your bards from becoming complacent and safely getting rich through bardi-ness. Remember, the best bard is a dead bard!