Travelling with sugar baby?

I have to come out and say that while I have considered travelling with sugar baby, and came very close to doing that once, I never have actually travelled. Would be very interesting to hear other people's opinions and experiences on this topic. Obviously one would need to know the other person quite well, in order to have a comfort level with them. Would we get the same room or separate rooms? After all we would spend at least a weekend together, so to keep things interesting we would need some down time.
I am planning two business trips this summer. One to NY the other to Chicago. Both trips are to network and catch up on old friends from a famous NY bank, who have now scattered to the winds.
Will probably fly in on a Saturday and stay for 3 or 4 days. would like to have business as well as pleasure on this trip. Let's just see how it goes. Play it by ear.

Anyway, eventually I decided to see the person with the injured puppy since she insisted she was telling the truth, and since she was responsive to other queries.

Also, she was barely 20, so that the image of young meat (or fresh meat like my assistant calls them) was too compeling.
So I met her, and oh my G*d she was so young, I look like her daddy.
But we had a nice relaxing lunch anyway, or so I thought at first. She had pretty bad table manners as in let's put our fingers in our mouth kind of manners. Also stuffing her face with nachos one after the other (and I am supposed to kiss that?!)
And then I asked why she is doing the sugar daddy thing. She replied that she is so short of cash she had to go to the pawn shop and sell her TV, Xbox etc. to raise cash. And she can't ask her parents for money because they are mad at her. She also said she was seeing sugar daddies to get back to her own father. Not sure what that means but anyway...
I didn't do anything with her for the following reasons:
1. It felt like I was robbing the cradle.
2. It also felt like I would be taking advantage of someone's financial misfortune. I don't know if there was enough chemistry there for her to be with me without the $. But I don't think so. So I really felt like a loan shark or something only in this case I would be charging sex instead of interest on the money. So I will pass on this one.
I doubt I will hear from her again, given that I didn't give her any gifts (so she wouldn't have to go to the pawn shop anymore).