Yo DH...yeah, I am great guy. I was a great guy when I was married to my X, I just got lazy and took things for granted, that and loosing my identity along the way combined with my X's emotional needs changing was the perfect storm. I don't have any issues with who I am as a person, I can look at myself in the mirror each morning and sleep like a rock all night long.
I do think though "The Coach" is more right than wrong when it comes to this new world of dating. So "Yes" you have made a financial commitment with this woman who seems to be or is wanting to date other people which should be fine since your not exclusive (you and her I don't think have ever had the talk) but in your mind it bothers you (or seems to bother you) because you have feelings for her and might want a relationship Which is why you "need some time" because it sounds like you started to fall for her (maybe her doing this hurt you a little????). So I think taking some time is good as you don't want her to see that your mad or angry or whatever emotions you are feeling. As we all know it is never good to place expectations on people as if you do you will always be let down.
So if you want nothing more than a physical relationship, or a phone relationship (essentially and EA), until you get to the vacation then I think you are going to need to reset your expectations of WG. Take it for what it is and as the coach says "Hang out, hook up, and have fun".........if WG wants a relationship from DH then WG will bring it up
Honestly just because you have made a financial commitment doesn't mean your locked in. Yes loosing the money would be unfortunate and I really do understand but don't let that financial piece put you in a position to sacrifice your own personal values, or accept table scraps from WG, or put you in a position of just accepting whatever she gives you. Which is why I think you need to reassess your expectations of her.
