Thanks for pointing out that recent post by Cheeky, I had missed it out.
I recall him saying that after Ep25 he would just have added a few short epilogues and maybe a short non-canon full-harem ending, and then he would have considered WTHI
finished for good and he would have
moved on to develop
another completely different game.
Thus any continuation of WTHI beyond those short epilogues was completely off the table at the time of that post I remember.
He totally excluded a regular length Ep26, let alone a Season 2.
He clearly stated that he had nothing more to add to this story.
Unfortunately he seems to have changed his mind if a Season 2 has now become an option...
IMO Ep25 was disappointing, "rushed" in storytelling nonetheless the long development time due mostly to the huge amount of slightly different duplicate scenes due to high level of branching.
The good idea behind WTHI has been already stretched beyond any reasonable limit, and ending the story with a cliffhanger (when it was clearly running out of narrative ideas) was an ass-pull.