So far I've got Alex (38), Jasmine (34), Clea (34) Yu (34), Zetta (31), Jordan (35), Teksab (32),Tsen (28), Boom (25)and Eve (25).
Buy a Captain Sword for Zetta if you haven't done it already. Then another one for Alex if you can afford it (sell all your junk and see what you get from it). Leave some gold to have 20 or more of the 4 main healing items.
Against Pride:
Jordan - Clea - Zetta - Teksab
If Pride boosts, have Clea nullify him. If possible make her fast using appropriate gears.
If your party has lost HPs, have Jordan heal with Surging Aura. Make sure his MPs don't get too low by using Magic Potion.
Against Luxury
Alex - Jasmine - Yu - Boom
Alex can cast Sing Along Lv 2 immediately. Target the spider first. Yu can cast Globe of Faith to protect everyone.
The 1,000 gold for a resistance trinket wasn't worth it
You got unlucky... there are other prizes. You could try again and see if it goes better.