I forgot about the "Accountant" trait. I think I will start training Adrienne then. She's one of those that hasn't been doing much in terms of training (mostly working as performer). But she is actually pretty useless in terms of stats. And yes, Armand is actually cheap compared to others.
My maids are all pretty high in Discipline because of the Head Maid, but they don't go over 60 Domestic, even if my Head Maid is 85 Domestic. They are all wearing the Maid Dress and I have Celeste Sunderland as Head Maid (I'm also trying to train her other skills). She is also my "Head" Maid in the morning, if you know what I'm talking about

I just finished training Adora to work as Head Chef. She gives us a nice boost plus 80+ Domestic reduces food by 1 per person. I have more than enough food with Barukumin and Zapin, but I donate to the Orphanage for the boost.
I've actually been starting to slowly replace my Janitors with high discipline Maids. It's fairly simple to get a girl working as maid with an outfit and raising her Discipline (easier and cheaper than assigning a teacher and doesn't occupy a teaching slot). But Janitors aren't really that important because it's easy to assign a few people with fairly decent discipline. There is no real high skill needed. I think the "job" could use a little reworking, but I still prefer to have high discipline people, mostly for fun. I think the max disrepair reduction is 3 per day and you can probably get that with about 60 discipline.
The tarvern is also pretty useless. Too little money for the investment needed. But I still like having one.
The workshop (or several workshops) to make guns and sell is OK. A bit "grindy" at times, but not too much.
I also think the game's economics aren't that great. I have all the business investments (I think), have a few people working at the academy and the shops, don't have a ridiculous amount of staff, have a fully working tavern and workshop (workshop set to sweatshot gets me 500-600 or 1000 to 1200 with merchandising). I have Armand and Rebecca doing their thing (Rebecca doesn't make me much money since I decided to wipe the gangs as much as possible). I also have 70+ standing with some factions. Defeated Mordecai and his gang (I currently have no title in the Republic)... and my daily net profit is only about 5.5k. I know, I can craft, sell scavenged stuff, sell extra food and all that (have 4 scavengers and 4 hunters). But the thing that makes me the most money is actually going to look for gold and gems around Kahill. With a little luck I find at least one Embryl per day (plus the rest of the gems). Haven't actually found any gems at the mine yet.
Mostly, I think the game needs some more reneable content, especially for after the main queslines. I currently have all the quests done and I'm in the middle of the Dengi Invasion. I think NWO is not overly difficult, but once you get to it, you probably have most of the quests done, if not all.