I was thinking along these lines, but wanted to wait and see what you came up with. A +2 Perform (any type of music/song/oration) sounds reasonable. Perhaps also a +2 Diplomacy bonus. I think that the bard would need to play for more than a round - perhaps 10 minutes or so before trying.
A 5Cp cost, with +2 Perform, +2 Diplomacy counds good to me, and I'll likely take it in the furture, depending on the direction of the campaign and how much experience Fredar gets with performing in the next phase of his career.
A diplomacy check would be my instinctive response. The RP could have a bearing on that. But as someone said, no one makes a thief RP their Search check, or a fighter their to hit roll.
Feat Option: (from the Modern SRD, Charismatic Hero): Charm - the hero selects one gender and gets bonus to any Cha skill role with a member of that gender. It can only be used on people whos initial attitude is indifferent or better. We could use something along these lines with a +2 bonus.
Humm, a good question this one. Thoughts anyone?
Here on the boards, it has generally come down to a debate between those who say bluf, those who say diplomacy, and those who say both. (As in, "Well, if the seduction is for the purpose of building a relaitonship, then it's diplomacy, if it's for mainly ulterior motives, then bluff."
I vote for diplomacy - bluff and sense motive may help, but I think they are are already taken into account via synergy bonuses. Further, while I guess I see the point about not having to RP the actual rolls for a bonus or penalty, I could see RP affecting whether Fredar gets himself into the situation where the roll would be granted.
I may take the charm feat, as I think it goes well with Fredar - do you think it's worth taking instead of dodge (that's more a survivability question than anything else. I'd like to take it but am afraid of being somewhat fragile bordering on useless in combat situations.
Gambling seems to be an overlooked area. Resisted Int check would be my intuiative call, at least for card type games. For horse races, maybe Handle Animal would be more appropriate. But I think its definately an area in which skill has a big influence. I think that it is doable as a skill - let me know what you think about the crunchy bits. Perhaps a Profession skill?
After a bit of searching, I found that Spycraft has some some of the simpler rules. Dice games are modified by sleight of hand, roulette and the like are not modified at all, except by cheating (Sleight of hand, DC 25+. Success=Allows 2nd roll, player chooses result to keep. Opposed by spot roll(s) to detect the cheating), poker and competitive games are modified by both Bluff and Sense Motive (Sleight of hand, DC 25+ to cheat, again opposed by spot rolls of opponent or other interested onlookers.)
This system meshes pretty well with Fredar (I might consider boosting sense motive a bit. Wis=7

) but if we go with something else that's fine, too: A Profession skill would make sense, with sysnergy bonuses from bluff and sense motive, cheating rules as above, for example. My question here would be th same as I had o nthe Charm feat above - will this be likely to come up enough in the campaign to make t worth spending the limited skill points he has on it? I defnitely want his skills to reflect his background, but also want him to be a decent candidate to join (and survive in) the Guard.