Re Maureen/Roger, theirs was such a fascinating dynamic. Maureen saw the good qualities in Roger, and while Roger didn't care about what the rest of Springfield thought of him, he cared about what Maureen thought of him. You could see hints of that when Roger and Maureen were trapped together during the blackout and when Roger visited Maureen's grave. Perhaps secretly deep down Roger might have been a little in love with Maureen but I don't think he ever would admit it or act on it. I think having Maureen turn to Roger in the aftermath of learning about the Ed/Lillian affair and Roger helping Maureen and Michelle leave Springfield and start over somewhere else might have played out better than killing off Maureen.
Looking at some older scenes on YouTube, the Great Pumpkin had an extra seating area beyond the swivel chairs as well as a billiard table (????), but that vanished in the great squashed set reset of 2020.
If the Grey Pimple was an additional hangout/meeting place I might have bought but for people to be continually hanging out there is dumb.