He is a Sankie , 100% and you are not his First ...
But do what you heart tells you if you need to , but follow the rule you just outlined. and he WILL ask for money , someone WILL get sick, and he will need $.
These males seek out jobs at resorts for a REASON.. to meet women like you.. They know who to target and how to play your Heart ... Deep down you know this ...
Surprise him by just showing up . See how that goes . If you tell him when you are coming he will just Pencil you into his Calendar ... he has MANY..
Do you SKYPE with him EVERY night ? If it were REAL that is what you would be doing , every single night after work .
as Others have said read Matilda's Blog ..
Lots of women have been through this ..