One of the things I have been writing about for some time is the positive impact of every players having multiple characters available for play. They can be if widely varying levels, but in my experience by the time you are on your 5th or6th session as a group of players everyone should have at least 2 characters each.
But how do you manage this?
Game Masters
You must keep strict records of in-game time! I have a very simple sheet that I use to track segments, rounds, turns, hours, days, and weeks during the game and I have a full in-world calendar to track - well, everything.
I also use party sheets listing every player, character, henchman, and prominent hireling that goes on each adventure. I put the real world date(s) of the sessions and add notes to the back about important, noteworthy, subtle, etc. events from the sessions on the back to add to my notes later then file each of these logs in a binder.
I also track what NPCs are doing 'off screen' and updated their notes and notecards as needed.
Players
The majority of character management has to be done by the players.
My players tend to use individual folders for each character. These folders contain their character sheets, character sheets for henchmen, and hireling log sheets, mount stats, familiar stats, and such. This keeps the things associated with the character in one location.
My players also take individual notes during each session that records the real-world date, tracks in-game time (not necessarily as strictly as I do!), and has notes on what players and characters were there, what happened, etc. Often in much more detail than I keep for individuals.
They also keep a list of objectives, enemies, friends, etc. so they can refresh their memories as needed.
Overall Management
You must remember that each player character is as different and independent as a henchman or another player's character. The 5th level magic-user that found a Ring of the Comet is not going to trade it for 4 Potions of Healing even if the other character is run by the same player! If players want to have trading and haggling done between their own characters they usually have the other players and DM 'sign off' on the deal to ensure everyone thinks both characters are being considered as individuals.
There you go! Simple effective steps to make multiple characters per player run smoothly!
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