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All seasons of the reboot series take place simultaneously.
Several members moved away during the original series' run, which we know isn't the first generation of the Midnight Society, and some of those who left town began new Midnight Societies wherever they wound up. This explains the totally different casts: The kids from Carnival of Doom are using the original site while the kids from Curse of the Shadows are part of one of the 'spin-off' Societies. Luke from Curse of the Shadows is also name dropped in Ghost Island. Sardo in Curse of the Shadows is the son, not the grandson of the original series Sardo
In "The Tale of the Super Specs" the original Sardo ended up stuck in a crystal ball, so his son was left in the care of his father. This explains why the Sardo in the flashback (which takes place in 1996, during the show's original run) is visibly much older than the original Sardo (allowing them to both be played by the same actor, Richard Dumont 20 years apart). Curse of the Shadows takes place in the same town as the original series
When the Midnight Society visits the past (which takes place in 1996), they see June Murphy expecting a call from Gary, the leader of the Midnight Society from the original series. Furthermore, Sardo, a recurring character created by Gary, is a real person in this series. Could it be that the magic shop that Gary and Kristen are seen visiting in the opening of "The Tale of the Super Specs" was Sardo's Magic Mansion? Dr Vink walks both the mortal and spirit realm
In his first appearance, having taken a ride in Flynn's cab, which, soon afterwards, fatally crashed, Dr Vink implicitly doomed the phantom cab to repeat its crash, until another traveller managed to solve Dr Vink's riddle. The bushes by his woodland cottage seem to imprison the spirits of hikers who failed. On investigation, the police find only a weed-strewn foundation; implying the cottage to have been phantasmal.- In his second appearance, Dr Vink is revealed to have been a film maker in the age of silent film. His version of Nosferatu projects from the screen a full-colour solidified version of its vampire. Might the suddenly solid vampire be a ghost of the film itself?
- In his third and fourth appearances, Dr Vink is revealed to have obtained a magical talisman from an obscure tribe, and to have pursued the ghost of a long-dead pirate.
- He seems to transcend material and temporal limitation, yet, as hinted by his bid to found some of his endeavours with pirate treasure, seems to be at least partly mortal. Might he be in a similar position to time travelling monk Brother Septimus?
Could the shopkeeper in "The Tale of the Crimson Clown" have built the dollhouse in "The Tale of the Dollmaker"?
Entrants to the dollhouse by a nearby attic door are gradually transformed into dolls. The slightly creepy ornament shop also has an impressive display of dolls. When pursued by the teleporting Crimson Clown doll, Sam dreams himself to be back in the shop, where, suddenly bound by an animate red ribbon, is approached by the shopkeeper, whose head is covered by a huge mask in the likeness of the Clown. Sam wakes in the dead of night to be cornered in his bedroom by a life-size version of the Clown, intent on punishing him for stealing brother Mike's money. Although Sam repents, and the Clown relents, might it have intended to transform him into one of its own kind?
Eric never left.
It's safe to assume there are plenty of Midnight Society meetings we did not see. Until the original Midnight Society disbanded, he simply came every second week, telling and hearing stories the viewers never saw. As The Friend Nobody Likes it simply wasn't commented on. The Sardo of Gary's and Tucker's stories is based on a colleague of their father
One who was somewhat infamous in the magic shop community for making up stories about his "real" encounters with the supernatural. The boys started imagining how he would react if he actually got involved in real magic, thus the Sardo stories of the original run. But what they didn't know is that he really did have some experience with the supernatural, as did his son. Max was a member of a chapter of The Midnight Society
When he goes to tell his story, he instinctively tried to submit it and also thought to throw something in the fire to make it go fwoosh despite only just meeting this iteration of The Midnight Society. Since the Betty Ann of this story is confirmed to be the same Betty Ann of the original Midnight society, that means she would've been around the same age as Max in 1996, maybe a little older. Maybe when the original Midnight Society ended, Betty Ann moved back to the island and started a chapter of the Midnight Society there. Captain Cutter from The Tale of Cutter's Treasure is a fictionalized version of Captain Cutter of Ghost Island and it was Betty Ann who gave Gary and Frank the idea for it
Betty Ann from Ghost Island is confirmed to be the same Betty Ann in the original Midnight Society. Based on Max's letter at the end of Ghost Island, we could assume that all the victims of the mirror got to keep their memories even after being released from the curse. This means that Betty Ann might have some memory of her time on the hotel and the true story of Captain Jonas Cutter. Maybe she talked about it to the rest of the original Midnight Society members and Gary and Frank used it as inspiration.