Assuming if the crtc rates are fair (lololoaoaoaqijlkahfalsdfasdf) and you can increase the quotas, they will be offered to both groups (the ones that choose to upgrade now, and the others that havent)?
And whats our quota for this month if we do the upgrade? eg, 200 gb or 150gb for the 39$ red package?
I think what you're asking is if we'd be upgrading the grandfathered packages with new quotas? If so, then no probably not - it would be sort of pointless since the new packages would have the same/higher quotas and faster speeds for the same price.
As for this month, if you change then it's the new quota.