By the way WotC has been stressing Unity and Bringing players of different editions together, I can only think of one way this can happen. This is by having two (or more) versions of 5th edition using the same math and created with official variant systems. I've mentioned it many times but my guess is a Basic Ruleset and an Advanced Ruleset along with 2 or 3 Variant Rules.
Basic Rules Characters: 2nd ed characters and earlier
Advanced Rules Characters: 4th ed Essential characters
Advanced Rules Characters with Variant Rule 1: 4th ed Traditional characters
Advanced Rules Characters with Variant Rule 2: 3.5 ed characters
If they use the multiple editions in one method, then there are some obvious issues to worry about.
Balance: Not everyone worries about it but many do. Some DMs will allow all version of characters in their games (isn't that the point). So each version of characters, and the races and classes within them, will need a "point" or "role" available to them. This will be difficult as Basic Rules Characters probably wont have many features (I expect HP, AC, Saving Throws, Attack bonus, Damage, Proficiencies, Spellcasting, and some Assorted "skill" bonus... that's it). These characters will have to compete with characters that have a bunch of bonuses and rules breaking/adjusting feature.
The Math: Somehow simple characters and complex characters with have to end up with close to the same numbers. The formulas for players who like simple characters will have to work with the formulas for players who like complex characters.
Conversion: Some people will convert characters form one set of rule to another. Some players will create basic characters at first to rule the rules and switch to another later. Or during RP, another set of rules might better reflect the character's progression in life. Therefore conversion rules will be needed and the process must be easy.
Basic Rules Characters: 2nd ed characters and earlier
Advanced Rules Characters: 4th ed Essential characters
Advanced Rules Characters with Variant Rule 1: 4th ed Traditional characters
Advanced Rules Characters with Variant Rule 2: 3.5 ed characters
If they use the multiple editions in one method, then there are some obvious issues to worry about.
Balance: Not everyone worries about it but many do. Some DMs will allow all version of characters in their games (isn't that the point). So each version of characters, and the races and classes within them, will need a "point" or "role" available to them. This will be difficult as Basic Rules Characters probably wont have many features (I expect HP, AC, Saving Throws, Attack bonus, Damage, Proficiencies, Spellcasting, and some Assorted "skill" bonus... that's it). These characters will have to compete with characters that have a bunch of bonuses and rules breaking/adjusting feature.
The Math: Somehow simple characters and complex characters with have to end up with close to the same numbers. The formulas for players who like simple characters will have to work with the formulas for players who like complex characters.
Conversion: Some people will convert characters form one set of rule to another. Some players will create basic characters at first to rule the rules and switch to another later. Or during RP, another set of rules might better reflect the character's progression in life. Therefore conversion rules will be needed and the process must be easy.