1) As ".ok" mentioned, the old Demi list is completely outdated and there is no way to track the others who earned them through the old method, so I find only giving them to people who we know for a fact earned them the old way would be completely unfair to all those who are not on the list and/or forgotten.
So as I see it, giving Demi awards to those who earned it through the old method cannot work as it would cause an issue with others complaining that they earned it but nobody remembers them, which would also probably lead to people falsely claiming that they had earned it in the past. Even if others vouched for them we could never really know for sure because many many people had modded it back in the day and might of fooled someone who would be vouching for them. Naturally/logically I would say we would be forced to only give it only to people who have unlocked it with the current method.
2) Robotic award cannot be compared to a Demi award because it's given to those who were awarded robo, so it's extremely easy to know who should receive the role, by definition we MUST know.
Though Demis are not possible to track so easily atm, the only way afaik to do that is to confirm it personally by joining a game and having them use a different skin and then watching them swap to Demi. (This is to weed out those who had set it as default avatar)
3) I am in support of a Demi award only if it can be 100% confirmed, but due to it's nature of being a total pain to confirm it would need to be requested, and then I'm really not sure who aside from myself would be willing to join games on request and confirm. Last option is to start looking at Craig to add something which would simplify the task, but then something as small as an award starts cutting into development time, which unless it takes two seconds to implement is not exactly ideal/realistic imo
4) How long would the award last? If Demi started getting modded on steam it would need to stop being awarded. And then we are left with the decision of wether it's really fair or not to have an award that others can never earn EVEN if they followed and completed all the legit requirements. Personally I'm against exclusive awards if others can still meet the same requirements as those already with the award and still not get the award.
So with that being said, I'm not sure what would be best to add but it's defiantly not impossible for it to work out, at least until/if it got modded. I can see why bob might not jump at the chance to add the award due to the trouble/pain it could potentially cause.
Right now it's only a role on discord because I'm confident that all those who have it are legit, Personally I have no issue with joining and confirming so I will continue to join maps and confirm upon request until/IF it starts getting modded. After that It will probably be removed unless we can think of something else, so hopefully modders don't ruin it for us.
If you notice something that could be done/said better in my opinions, or if i'm missing something like how to confirm others using a better method please point it out to me.