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When a player plays a very complicated character, such as an artificer or (say) a bard/druid/green whisperer/sublime chord/arcane hierophant, this can impose extra work on the poor DM who has to understand how everyone's characters work. Assuming that the DM is fundamentally willing to deal with this complexity and that the character isn't otherwise problematic (e.g. overpowered), that DM might still appreciate the player going the extra mile to keep the complexity from getting out of hand.

Some things are obvious: if you are playing such a "snowflake", then you should make sure that you know your character front to back; the game should never be waiting on you to figure something out. Another thing is flexibility: when the rules pile up, the DM may need to handwave to keep things moving along.

Having a sort of DM-oriented mechanical summary might help. If you're playing a barbarian of a certain level, the DM will probably have an intuitive sense of what the character can do. A half-page or so outlining key capabilities might be helpful.

One idea that occurred to me, inspired by various LARPs, was to pair mechanical complexity with metagame requirements. For instance, playing an obscure bloodline or using a rare discipline might require that you submit a longer backstory. In D&D 3.5, there are plenty of things that might trigger such requirements, such as prolific multiclassing or uncommon subsystems (e.g. psionics). This could also be used as a worldbuilding tool for a non-standard setting: if you take an ability with a regional requirement, you must write a brief description of the region you come from that provides context for that ability.

I'm looking for ideas from players and DMs, but particularly from DMs who have had players bring convoluted characters. What went well, and what went badly? How could that player have made your job easier?

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    \$\begingroup\$ It seems to me that you are trying to talk about 2 topics 1) How can the player of a complex char help the DM with game mechanics 2) What requirements should you have for the player. It would be better if you focus on one thing or tell us how are they connected. \$\endgroup\$ – Baskakov_Dmitriy Jul 18 '17 at 15:51
  • \$\begingroup\$ I second @Baskakov_Dmitriy: The requirements for backstory are completely different from the mechanics involved. \$\endgroup\$ – Matthieu M. Jul 19 '17 at 12:02
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Speaking from my experience here, there are a couple of things I would recommend:

  • DM Cheat sheet - this was really helpful for me, since it gave me an idea of the basics of the character. I made sure the player created and provided me with this sheet at every level, not only to keep me informed with what their character was doing, but also to give me insight into what they thought was important about their character. This helped me to build obstacles that catered to their character's specific role, or at the very least what the PC perceived their role to be in the party. I would limit this cheat sheet to 1/2 a page at lower levels, and 1 page at higher levels, to ensure it remains concise and useful to the DM.
  • Time Limit on turns - this was a more controversial move in our group, but definitely helped keep my PCs on top of their characters. If I as a DM had a question, or asked their character to do something, the complicated PC would have no more than a minute (or 2 depending on how complex the request was) to figure out the answer. By having the PCs aware that this time limit was in effect, it incentivized them to maintain a deep understanding of their character. Our table also had a high level of trust, so I wasn't too worried about my PCs fudging their characters in these time sensitive scenarios.
  • In advance verification - this was something I only used once, but can still highly recommend. Before allowing my PC to create a complex, multi-classed character, I sat down with them and discussed why they wanted to create such a character, and how we could work together to streamline the process in-game (this was incidentally how we landed on the cheat sheet solution above). By having this talk in advance, you can understand why the player wants a convoluted character, and brainstorm alternatives if possible (eg Player: I want to be a healer, but also be able to fight. Me: well instead of multi-classing and trying to use 3 prestige classes, you could just main as a Cleric, and by taking feats X, Y, and Z still achieve this goal). If alternatives are not an option (eg Player: No, I really want to play [insert convoluted character]!) then at least you've now gotten some perspective on where they are coming from, why they have chosen this particular build, and laid the groundwork for future discussions should things go off the rail.

Introducing a metagaming requirement is an interesting idea, and something I had not considered. While this would be useful in the context of the game's lore and the character's development, if you are more concerned about how to deal with complicated characters as a DM, I would just warn you that complicated backstories can lead to complex character motivations, which in my experience, often leads into My Guy problems.

That being said, the flip side is that you are maximizing the number of plot hook you as a DM have available. Is the character adamant on being a bard/druid/green whisperer/sublime chord/arcane hierophant? Fine, but their complex background has made them a target of a group of purist druids, who believe their magics are being abused by an outsider for their own personal gain.

Ultimately, requiring as comprehensive a backstory as the character is complicated can work both ways, but independent of this, I would advise you to consider some of my suggestions listed above. They can definitely streamline the DM process, and make your life a lot easier.

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    \$\begingroup\$ This is a decent answer in some places, but I have to give it a -1 for implying that enforcing metagame requirements on character building and multiclassing is in any way a good idea. I feel that that results in something generally adversarial, as opposed to the ideal situation of working with a player to make their character the most fun for both them and the DM as possible. \$\endgroup\$ – Forrestfire Jul 18 '17 at 17:02
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    \$\begingroup\$ @Forrestfire Ultimately I think it depends on the dynamic of the group, and the type of game the PCs and DM are interested in playing. All things being equal, I can see it both working in some situations, and not working in others, hence my covering of both sides of the suggestion \$\endgroup\$ – B. S. Morganstein Jul 18 '17 at 17:33
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    \$\begingroup\$ @KRyan Fair enough. I still think there are situations where requiring a player to develop a thorough backstory could be useful, so long as the player does not view this as a penalty for developing a complex character. Again, I think it will all come down to the specific group, their goals, and their expectations for a fun game \$\endgroup\$ – B. S. Morganstein Jul 18 '17 at 17:47
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    \$\begingroup\$ Encouraging expansion of backstory and tying it into the campaign setting is good. Punishing players for enjoying the system's intricacies by enforcing these things is not. This sort of handling promotes a relationship between GM and player analogous to a parent and child who's done something wrong, rather than a relationship between equal peers. So no, I assert that there is never a good way to implement such a concept. Simple discussion of goals for backstory writing, and genuinely tying backstory concepts into the game in good faith, is enough. \$\endgroup\$ – Forrestfire Jul 18 '17 at 19:21
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    \$\begingroup\$ Oh certainly, thorough backstories are often good. But the question is rules tying extra backstory requirements to the mechanics chosen to represent the character. That is, by definition, punishment. Punishment is what was being discussed. Encouraging all players to have a solid backstory that matches their mechanics is good, just not what was suggested. \$\endgroup\$ – KRyan Jul 18 '17 at 21:16
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It's not easy

I have played a few such characters (both in 3.5 and PFRPG). I remember a Fighter/ Paladin/ Ranger/ Hospitaler/ Knight of the Chalice/Wild Plains Outrider, Cleric/ Contemplative/ Ruathar/ Sacred Exorcist, Bard/ Rogue/ Temple Raider of Olidammara and a Cleric/ Wizard/ Mystic Theurge/ Contemplative. The important things I learned:

  • Be ready to answer question by providing the source material to the DM I had photocopies of my stuff.

  • Don't argue if the DM makes a ruling. Roll with it and discuss it away from the table AFTER the game (though point #1 generally helps)

  • Too many abilities means you will forget stuff You will. Knowing your character is one thing, but remembering all those bells and whistles, especially in the middle of the action will happen.

  • Simplify your character sheet. I moved to using stat blocks years ago because it simplified my life and GM could quickly review.

Just some notes.

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