Well to answer some things For 1. Dyne asked on Patreon or twitter I believe and most people answered that they didn't want bad endings or at least if it is a bad ending let it make sense. I could be wrong but you can think of it as the "bad" ending is not actually bad just not the best outcome. For 4 and 6, Maria can not be romanced as the mc is gay and so is the focus of the Visual novel I think. As for Richard and Maria love story its not the focus of the novel so it may just appear from time to time in characters routes. Dyne also stated that just because a route has finished doesn't mean the character is, he may make little shorts or whatever he may plan. Like he can make a little short where you go on a double date with one of the romanced options and the other couple would be Maria and Richard, but im really unsure. So far the only route done is Harold/Coach Grifter/Papa Bear.