An update: I've been playing James Skylark for a while and he's developing well.
From a mechanic/combat POV, he has good defenses. With a mithril chain mail and a wand of Shield he can get to AC 22 or so. I expect to gain better armor by the time the wand runs out. If things go bad, I have Expeditious Retreat, Levitation and Invisibility. I also have a modicum of healing capability via potions. In fact, I think the DM hates the way I always seem to have the situation under control; I'm sure that I'll somehow have to fight hard for my life in the next couple of sessions.
He's not that well equipped for offense, though. The shortbow rarely deals useful damage and the spells' saves are a bit too low. Since many of them are all-or-nothing spells (charm, glitterdust, fear, that sort of things), when they do hit they hit hard, though, disabling or severely hampering the opponent. I have spells that target all saves and I use them effectively.
Plus, we've been in a couple of large-scale battles where the bardic song ability was extremely useful. I'm going to get the Requiem feat ASAP, of course, and I'll probably try for either that PrC which grants extra bardic songs from S&S, or an archery-oriented one. The DM doesn't automatically allow PrCs, having characters seek a trainer for example, so I'm keeping generic and waiting for an opening.
Besides, I also can't wait for the bard changes in 3.5E, which apparently will allow me to forsake the 10% arcane failure check I'm suffering now and to get some more skills.
From a stylish/roleplaying POV, he totally dominates!

He makes a liberal use of magic in everything he does - from using the percussion spell from S&S whenever he introduces himself, to using prestidigitation to comb his hair and dry his clothes. Think Simkin from Darksword. In fact, I want to get an item which allows for permanent prestidigitation... that spell is just too cool.
He's an ungodly braggart, backed by his uncanny ability of dealing the last 5 points of damage to the monster after the rest of the party brought it to 2 HP. With the high CHA skills he has, noone can do much to contradict him. He likes people being happy and is a master at improving morale. Noone has ever fled a battle when he was around.
He hates when he can't talk to an enemy. The party recently met a water elemental, and since only the obnoxious 8-CHA wizard spoke aquan, James had to sit nervously aside, fervently pray that the elf didn't say anything stupid, and interrupt every few seconds to have her explain him what was going on. He's going to learn Tongues ASAP.
As for the future, there's some reckoning brewing. An NPC mentioned a black dragon of undefined age in a nearby swamp, very close to where our town has to mine coal. The dragon doesn't seem to have noticed or care for us, but I can see all too well where this is leading. What's worse, the bard specifically brags about killing shadow dragons, and the NPC only said that the dragon is black in color, so... uhm, and protection from negative energy doesn't even work on Ravenloft...

Ah well, I don't have enough info to make a plan yet.
Anyway; a magic items merchant has become available and will be for a while. I don't have much money, probably around 1000 gp or so, certainly not enough for useful permanent items. Suggest me some useful low-level scrolls, wands or potions that I might want.