@toucanbuzz Sounds fun! I'm curious, what does your "Boasting" prop look like?
These were heavily borrowed from Paizo forums for the Kingmaker "War of the River Kings" module. There is one competitor not listed who is from the host city-state that customizes a boast about being a spy in the PC barony and uncovering all sorts of sordid, outlandish secrets (e.g. in our campaign, a graffiti artist paints the walls regarding lewd acts between the Baron and Stumpy, the town's 3-legged dog). Because of this, the script varies. It's also custom the host-nation loses the overall tournament competitions, so their "champion" tanked it despite being a skilled orator. It's expected as there's a magical item reward from the host city-state for winning the week-long tourney point total.
PC rolls randomly to see which order they go in.
I had players pick, based off a mild description of the boast, who they wanted to enact, and roll the checks. Each Boast has 3 parts: beginning (introduce yourself as someone to be respected, Intimidate check (can use CHA Score), middle (the fun stuff, Bluff), and end (finish in style, Persuasion). The DC is whatever sounds good, but I went with 15. At the end, every performer rolls a Performance (CHA) check.
Because cheating is allowed (it's only illegal if you are caught), one performer gets a +5 to all checks if his bard friend isn't caught roaming the crowd casting helpful spells.
Tally the # of successes (e.g. 0 to 3). Then, multiple this by the actual Performance check. If you had 0 successes, then final score is 1/2. At that point, you're probably salvaging pride and something about the story didn't resonate. Badly.
Highest score wins the heart of the drunken crowd.
Since it was the group's first time at a Boast, they didn't have time to script anything. That's fine. We summarized the gist, audience reaction based on rolls, and played it that way. Because he'd been magically boosted with Enhance Ability, it wasn't too close.