So our latest campaign, Operation: ANTIQUARIAN has just come to a dramatic and rather final end, with one PC obliterated from the universe by the Great Old Ones, another reduced to a SANless husk, temporal distortions, people literally wearing other people's faces, a complex Cold War nuclear gambit aimed at bringing about the apocalypse, and oh yes, two PCs who are basically more or less fine actually.
But this is not a time to evaluate that scenario, it's a time of change. For with the end of that campaign comes a new one, and that new one is of Oliver, and it will be Planescape!
In case anyone's reading this and doesn't know what Planescape is: it's like The Faraway Tree, except Dame Slap is replaced by an omnipotent theocidal regent* called the Lady of Pain, the Tree is a city called Sigil built on the inside of a torus hovering over an infinitely tall spire, the place is populated with gangs and sinister philosophical guilds rather than happy elves, and you can never run home to mother ever again.
*I was going to say "with a strong BDSM vibe, and then I thought, y'know...
So obviously we had to come up with character concepts, for a 3rd-level character, and naturally the first thing that came to me was a Gap Yahoo or a spoilt Elven Prince(ss) (I have prior form with the latter). Then I thought, obviously, combine the two. And thus, after much toing and froing about builds, it was done.
The problem I had wasn't mechanical, but simply how the heck do you go about building "gap year traveller" in D&D 5e? It doesn't lend itself very obviously to any class.
Building a Gap Yahoo
There are two immediate contenders for this build: Bard and Ranger.
Bard is the Word
Bard offers a vagabond life (good), lets you pick up a bit of everything rather than having any strong (ideal) and has some good roleplay points. It lets you pull out a guitar/bongos/really authentic traditional noseflute at the slightest provocation and force people to listen to you, and know all kinds of random stuff because you heard it from a gnome this one time.
The problem with Bard is, I hate the mechanics. This continues my near-seamless run of bard-hating throughout editions of D&D. Ironically, this is the first where I hate the mechanics rather than the entire concept of the thing, since the "sing at people during fights" bit is significantly downplayed.
Essentially, bards boil down to four things. They can fight a bit (like everyone) and they can cast some spells (like most people). They can sing, granting Inspiration Dice to allies. And they're generically good at stuff.
Unfortunately, they feel really bland to me. A very substantial part of the bard's abilities seem very passive, so that I don't think they'd feel very satisfying to use. They can improve the rate of healing when allies rest, which is laudable, but feels a bit dull - it's essentially a flat bonus to the recovery rules. They get bonuses to various skills, which is also nice, but in my experience you don't particularly notice that you've got it. The fighting is fine, though without any particular schtick in combat I feel they wouldn't be that interesting to run. Spells you can do something with and use actively, I don't deny that.
Inspiration dice are a problem for me, because I think they're really faffy. They almost seem designed to bring the game to a crashing halt. The problem isn't with the idea (you inspire allies, they can roll an extra die when they need it) but the implementation.
You use a bonus action on your turn to choose one other creature within 60 ft. who can hear you, and give them one Bardic Inspiration die. Once within 10 minutes, the creature can roll and add this die to a check/attack/save. Two archetypes allow you other uses for the die, either penalising an enemy, or adding to an ally's damage or AC for a single attack. In all cases, the creature can use the BI die after taking the original roll, but must do so before the DM says whether they succeeded or failed.
I'm not sure whether this will seem like a problem to others, so let me explain. This rule creates a whole set of decision points, and calls for weighing up odds and metagame knowledge in-game. These sorts of things slow the game down and can be stressful to decide.
Firstly, you must decide when to allocate a die. There's a fair bit of resource management in D&D, but this one involves a fair bit of guesswork over who's likely to need your dice. At early levels, you only refresh your pool after a long rest, so misallocating a die to someone who doesn't need it is a substantial loss.
Secondly, actually using the die is fiddly, because it must be used between rolling a normal die and declaring the result. This seems like it will slow down play while the player ponders the odds. Is this a decent roll? Do I care about this action enough to consider spending a BI die to potentially adjust the result? What do I think the chances of success are, anyway? If I succeeded anyway, I'll be wasting the die, so is it more important (in the light of what I currently believe my chance to be without the die) to boost my chances of success here or to keep the die in reserve? What are the chances that spending the die now will actually change the outcome of the roll? How level-appropriate is this challenge? Does this critter look particularly tough, or strong, or vulnerable to fire? Because the calculation has to be done between roll and result, everyone needs to pause whenever a roll is made involving a player with BI dice. The DM can't resolve the result until the player decides whether they might want to adjust it. It's likely that several players will have the dice; as they have to be allocated on the bard's turn, you need to buff people in advance, and it may well be several turns or minutes before they use their die.
It's worth noting here that we play online over Ventrilo. Around a table, pausing to check whether someone wants to adjust potentially quite a large proportion of the rolls is at least fairly quick. Over Ventrilo, it's often difficult to tell what's going on. Lag, inability to actually see other players, and other issues would make this mechanic more of a problem. In essence, you'd need the DM to wait for the player's "pass" or "use BI die" whenever it might be relevant. And you can't assume the DM will remember who has dice when. Then you get the bit where everyone's waiting for someone else to respond, or wondering whether there's server issues. Quite likely, you'd end up wasting a lot of time on this, and pacing would plummet.
Thirdly, it's a bit subtle, but this mechanic (in most iterations) shifts agency from the bard player to the ally. You don't get to choose what happens, you give your mate some power and they decide how to use it. In a sense, it's doubly passive: you're trading a buff ability against the chance to smite enemies yourself, launch spells, and suchlike. However, when you actually use it, you don't get the satisfaction of making the blade strike home, the ally vault the chasm, deflecting the spell or whatever. You give someone a potential to at a time of their choosing get that satisfaction. Personally, I don't think I would find it a very satisfying mechanic to use. There's also a certain danger that, like the cleric and other buffers, you end up not making the decision yourself, but being told who to inspire when (it's optimal for the party, right?).
Fourthly, I don't like the sheer weight of metagame in using these dice. Resource allocation always involves a little bit of metagaming, but this power revolves specifically around making OOC judgements about the likely success of a die roll based on your estimation of your own success and the mechanical difficulty of the challenge.
This isn't to say you couldn't have fun playing as a bard; I just felt very uninspired by it, as though the fun would tend to come from things other than making a useful mechanical contribution. I have a character for that already. And I felt Inspiration Dice would gum up the works. So I passed on Bard.
I'm particularly puzzled about the Inspiration Dice mechanic, because there are other slightly similar rules in play which are more elegant. Battle Master fighters can spend Superiority Dice to perform manoeuvres, use special attacks or direct their allies. Monks and Sorcerers get pools of points to spend performing special actions. None of these involve interrupting a roll to use the ability, nor handing off the ability to an ally.
At the most basic level, if Inspiration simply gave you a reroll it would be negate most of these issues. There's minimal metagaming involved, just a decision whether trying again is worthwhile; with knowledge of your first attempt this is a fairly simple decision. You don't interrupt rolls, so it doesn't slow down the game any more than any kind of reactive ability - you just carry as normal unless someone states they're rerolling. If rerolling seems too powerful, maybe use a die to trigger Advantage/Disadvantage? Grant a static bonus but use before rolling? I don't know the exact balance issues. The point is, these would be more elegant mechanics.
For someone who travels around a lot, Ranger sounds like a good starting point. In fact, though, this isn't really true. The fluff and the crunch for rangers both make it clear that they're quite specialised and tied to particular situations. They get a favoured terrain type to inhabit, and that doesn't include "urban"; a ranger will be slightly weaker in games set in cities, or where you travel a lot between different terrain types, or set mostly in a different climate, while they'll be quite strong if the game ties in well to their favoured terrain. They're also supposedly dedicated to defending certain areas or to hunting down particular monsters. The level of focus here didn't seem like a great fit for my lackadaisical Gap Yahoo.
No mechanical complaints here (other than the lack of "urban", which seems a shame) but it didn't quite fit my needs.
The obvious solution to having no idea what to do was to multiclass.
Based on an early remark of Dan's, and the Trustafarian Gap Yahoo image, I got quite invested in the idea of being a Draconic Sorcerer. Why? Because few things say privileged and Special Snowflakey better than having a Gold Dragon for a grandfather. An elven princeling with draconic heritage is just perfect. You can swan around in robes, you don't need to do any hard work for it or particularly learn anything... ideal.
On the other hand, I wasn't sold on being a sorcerer per se. A minor point was that it still felt maybe a bit too focused for what I'd envisioned. A much bigger one was that I'm already playing a single-classed Charisma-based arcane spellcaster in another 5e campaign. Charismatic characters tend to default to being the party face (and therefore picking the same skills), tend to be pretty frail and not especially keen on melée; you can differentiate them of course, but I felt like this would be a bit too similar.
Flicking through the book, I thought about the Monk. The monk picture seems, to me, very very Gap Yeary. The woman pictured, to my jaundiced eye, looks exactly like she's taking part in a really traditional authentic meditation practice she learned while she was backpacking in Burma that's actually really spiritual actually. Randomly deciding to learn some meditation techniques, martial arts and a few superficial bits of culture in your travels is very very appropriate.
Plus, it seems to me that Monk and Sorcerer synergise very well. Both work best unarmoured (although a low-Dex Sorcerer in heavy armour is actually viable in 5e), with a good Dex score. Neither needs much Strength. A Monk-Sorcerer can use Dex to attack reasonably well in melée and at range, and is a bit more resilient than pure Sorcerer. Plus, as a Draconic Sorcerer you can pull off some very nice synergy: moderate scores in Wisdom and Dexterity, plus your inherent AC13 for being scaly, gives you an AC17, which is as good as most fighters can manage! A low-level character is very unlikely to get a stat of 18, and if you did, you'd want to spend it on Charisma anyway as a caster. This build allows an array of solid-but-unamazing stats to work in your favour.
I was still very hazy about this concept, though. Was the multiclassing just going to make me incredibly suboptimal? Was this a daft idea? Should I start again? Around this point, Arthur suggests that if I'm feeling undecided, why not consider just taking a class to represent whatever I was being prepared for by the family?
I couldn't really think of any class that says "parachuted into well-paid corporate role" (or the equivalent), but I eventually decided that an elven princeling is stereotypically trained to patrol the borders against orcs. That means ranger or fighter. For a while I considered rebuilding my character from scratch as just a fighter or ranger build, but it didn't fit the background I'd come up with.
In the end, I decided to just throw myself at this concept, and I built a triple-classed character. A Ranger/Sorcerer/Monk, of all things. Our princeling has basic training as a ranger, is a sorcerer by heritage, and after setting out on his travels, has been really getting into exploring his spirituality actually.
se'Acharvol-édhí Fonsásithali'us (call him Charlie) is a scion of House Sílháendr of the Dawnpeaks, in shining Únala - which is, depending on your perspective, either far-flung and a faint rumour, or the only significant place in the multiverse. He is of a truly noble line, for his grandsire was Garthaphas, the great golden dragon of the South, and the blessing of the dragon lies heavy upon him. Like any princeling of his line, Charlie has been raised to war, to the maintenance of the mountain borders against the foul things that stalk and slay their people. Hunting, stalking, the ways of sword and bow, all these he knows. He is schooled to wield the magic that is his heritage, and use it with due restraint. An array of noble tutors have striven to bring him the accomplishments due to one of his blood: chess, watercolours, cross-stitch, the art of fan and flower, the lute and the lyre, the harp and hawk, the gavotte and pavane. In these matters, their success has been a little more modest; and yet it will suffice.
A grand future awaits Charlie in the service of his people. A half-century of schooling at the Silent Academy will grant him all manner of wisdom, arcane and philosophical; a mastery of discipline and diplomacy, an unparalleled knowledge of the Old Times and the Prophecies of the Times To Come. Beyond that, tempered by learning, he will take up a high position in the Court of the House, serving at the hand of his mother, the Lady Meáilith. It would, after all, be unbefitting for one of such noble blood to work his way up.
But before entering upon his training, Charlie has taken the Path of the Exile. Breaking free from childhood, not yet truly an adult, he has left the land of his ancestors to wander amongst the realms, testing his skills and his character against the challenges of the worlds. After a few decades, hardened by travails, with a mind broadened by encounters with many folk and many wonders, he will be ready to take up the reins of learning once more. He has sailed on seas of shining scarlet, and crawled through forests of bone. He has served with questing knights, and behind the humble bars of rollicking taverns. Quite a lot of taverns, actually. He has spoken with the farmers of Faerûn, and the barbarians of Icewind Dale. In sun-cursed Athas he studied with the thri-keen ascetics of the Silt Sea, which was really amazing, just this incredible sort of spiritual experience. In bustling Cyre he had his portrait painted in front of many monuments and hung out with some brilliant warforged conservationists. His journals, transmitted to distant Únala by magical means, brim with profound encounters and moving scenes. He is thinking of writing a book about it all when he returns.
Unfortunately, Charlie is currently a little short of the ready. Natch, Mumsie gave him a few grand when he started out, but getting to Athas was quite pricey actually. Then a few years ago he met these gnomes during a gig, and they were dead set on going to see Shou Lung, but there was a bit of trouble there and it was rather expensive. Then someone suggested an expedition, so they bought shares in this old caravan sort of thing, it was amazing, and just sort of decorated it with meaningful motifs, and they went round doing circus tricks and teaching a bit of Elvish in a few schools. They were going to go to the Feywild, but they ended up doing a few detours along the way, and then he ended up hanging out with an orcish accordion band, and...
Well, have you been to the Elemental Demiplane of Hemp at all?
So anyway, what with one thing and another, bit short of the old cash right now, thought a spot of adventuring sounded like a lark.
Charlie is a shade under 6', average build, tanned, with dreadlocks and a few multicoloured streaks. He has purple eyes, patches of golden scale, and a tattoo in Celestial that an aasimar sailor promised him meant, like, Supremacy of the Spirit, even though devas occasionally giggle when they pass. He carries a staff he bought from a really traditional gnomish staff-carver in the caverns of Gnarblos, and a huge rucksack full of assorted junk and souvenirs. Lately, Charlie has been getting really into retro-nouveau genasi abyssal post-funk jazz.