What to do with winners that have not activated / multiple wins or both

if reroll is denied, it's denied. i would advise sending them gifts.
if you want to limit that in future, check out sgtools

The 1 month thing only means that if the winner has broken the rules within the last month your reroll will automatically be granted even if they have already been punished for it.

If they haven't been punished yet the reroll will be granted even if the infractions happened 5 years ago.

It's just a matter of poor wording
Infractions don't expire, but stop counting once a user gets punished for them in which case the request will get denied.
Basically if punishment hasn't been served yet any infraction results in a temporary suspension and a reroll. When I once inquired about the time limit I was informed that for example somebody might just get a few days long suspension for a minor infraction, but still it's possible to request a reroll for the specified time(back then it was 2 weeks) It's an old interpretation, so if the rules has changed, please correct me.

Long story short. Just make a reroll ticket. If it gets approved it means that the user somehow avoided being punished till now. On the other hand if it gets denied it means that the punishment has been served before.

thank you everyone

though i think its a miss that you cant view older infractions
that would offload lots of work from support