i don't think its that far in the future, Maybe a bit more then Dimi initially planned (because the chapter final keeps getting bigger

)
as far as i know the main narrative for season 2(?) will center around the district the foxbox is in Whit mayor de pasto(jessy bio-father) planning to re-zone it into a shopping district (probably due to some back room deal made whit campaign backers)
there will also be long-term things like: new club president (as stan will most likely not be around for season 2) ,becoming a full patch member off the club
other side things like : the already mentioned baby boom for the harem,possible problems from Rin's past or others ,other Club trying to move into the void left by the minions, revenge from a other minion chapter.
Dimi can take many roads in writing the next part off story
Maybe some off the things i mention will already be in the upcoming updates before season 2