Thaila would be good to add. You have 5 goddesses with him a huntress and a demigod. Plus I think hades and zues reactions would be funny.

Annihilape, espeon, umbreon, golem, machamp and riachu

Whitney, roxy, gardenia, skyla and courtney

Healers I know of are angels Asia Valerie le fay and kuroka and koneko with senjutsu. So most yokai should work. I think ingvild has healing magic but not sure. Also as angels have healing and purifying powers it should be possible for fallen angels to have it aswell

Give him only knowledge of season 1. So he knows upto end of riser arc. That way he only knows a few characters and it'll be more entertaining

I liked this so please finish it

Sophia Turner or scarlet johanson

I go with dead. Kinda feels like it's to messed up. The plot is so far of the rails that the world is screwed as rias and issei won't go to save yasaka in kyoto so great red appears and world destroyed

Monica over OC. Phoebe would be interesting though

Loki would be my pick but if he is going solo then heaphestus

I'd go treecko for grass, charmander for fire, bellum for psychic, ralts for fairy, elekid or shinx for electric, larvitar for ground, bagon or gible for dragon, gengar for ghost, dratini for flying, aron for steel, riolu for fighting, geodude for rock, umbreon for dark, nidoran for poison, glaceon for ice and scyther for bug. I think that's all the types but I may have missed some.

Charlotte, noelle, Rebecca, Vanessa and the girl with sing magic from water temple as love interests

Mordred, medea and atalanta would fit well. You get an archer, a mage and a swordsmen. Plus interesting interaction with mordred and artoria. I'd also remove xenovia and add either medusa or semiramis. Xenovia is better in rias peerage as a Knight as pawn is wasted on her lack of magic and technique. Unl8ke irina.