Congratulations. This is a great game. You have evolved it into a story-telling work of art. I enjoy it, I enjoy the challenges it poses, and the rewards it provides. And it is sad to lose a character, or have to release a character. So well done.
The up to six member special dungeon dive makes me want more, as do the quests. I am not familiar with the football manager game, but I am familiar with various DND type systems, and I think you could add more DND flavor without losing any game flow.
The thief/assassin character type feels like it could fit into the DPS group conceptually, but I can't speak to the actual fighting screen tactics. You do have skill checks, and perhaps lock picking/door opening could be added (no thief, no chance). I always want more money, and you seem to want me to want more money.
The game starts with 'the king is dead we have no king' but does not end with 'you have been offered the kingship' - instead I get to the top of the competition mountain and try to stay there. Let me add that is quite a challenge with retirements and the damnable dangerous wars, so don't change that. But am I supposed to try for the kingship? It seems a popularity model, or a multi-sector of the populace model, could add something. Nobles, merchants, hoi polloi, lowest class. You already have a reputation mechanic. Here is another possibility to drain my money.
Arcanists don't get enough love, although the party-scorchers certainly let me know when they are there. How about arcanist-based quests and dungeons or tasks? Arcanist skill checks could be very interesting. A high enough level (or skilled enough arcanist) should be able to travel or portal - astral travel, elemental planes, other planes, could create post-20 leveling or challenges. Once your characters are 20/100 they are plateaued (for obvious competition reasons), but that need not be a limit. Why can't I craft a group around an arcanist or two and have them on some really wild dungeons or quests? And I want a magic user that is more dangerous than the worst tamed monster - they should be. In any DND type system, the most dangerous character is the high level magic user.
Some clerics should be able to do the same - a quest into the levels of hell with my paladin and cleric? Sign me up!
Sages could be retired arcanists. By the way three types of cleric (which are great) makes me want arcanist specialists (sorceror, psionicist, etc.) which could then be staff (or hire on staff). I think potions and scrolls don't work, but more character equipment locations and magic items to match could be interesting.
I guess I want more, more and more. Great work!