Her disappearance wasn't scripted here(the game probably glitched then fixed itself)just focus on lowering her trauma for now and then work on increasing her confidence.
As for Bailey,you can fight him thrice?(i think),after which he brings 2 thugs with him which is a scripted loss,you can circumvent it by triggering his 4th visit at Alex's farm but you will have to fight both his and remy's thugs
.
Money early-game can be easily acquired by working at spa,modeling and treasure hunting(some Bozo's here might try to shill you Cow tf line,just ignore them.)