In my POV your examples do not answer the medium problematic. Tabletop versus online. Of course communication and calculations are involved in both mediums but because the mediums are different they work in a different way. In tabletop rpgs the factor of direct human communication is a mechanic of the game - in-game. In MMOs this is not the case. So if you build for tabletops you have to expand on this mechanic. OTOH in MMOs you have to build feedback challenges by a pcomputer program. Then you compete and/or value performance of people on these challenges. This is very different than human communication experiences which is something inherent to the way we value reality.
Having said that, you see that guilds in MMO serve a vastly different purpose than your parallelism of inserting guilds in the storytelling or narrative instance of tabletop rpgs. Regarding roles: you assume that in tabletop D&D they are a principle. I can accept this. But I cant accept that in tabletop they have to remain stable as a principle. As a guideline, perhaps yes, this is true. But each player each moment serves a different, his own purpose or role. These roles or purposes are not permanently stable. So they are more casual we could say. OTOH in MMOs roles are mechanicaly stable because things are limited by the fact of the artifical program. Now, instead of caring to limit things I would try to build and expand on the actual strengths of the tabletop medium to make players happy, to enhance their enjoyment and "fun" with the tabletop game. I would alter the way combat works in my D&D regarding character creation and the actual combat mechanics to suit the tabletop's strengths -I would rather build it like a dynamic programm that can reprogram itself with each player's input -rather than building a system that has to conform things the other way around.But this is just a thought. Regarding monsters and threats I would try to expand this more dynamically. Rather than focusing on one kind of goal (fight monsters) I would introduce mechanics for how permanent strategic goals are formed or modeled (love relationships, honor-duty, revenge, stuff like that) aside from casual action. You are talking about other media but isnt't it what I describe here more akeen to the storytelling we find in them?
Anyway, I hope even if you do not agree that I managed to explain myself in a way that you can see my POV.