.... not many people can..., or are willing to spend $ 2000 for a night in a nice hotel accompanied with a WL...., I certainly wouldn't.
In some ways, I think it's about trust and if the lady genuinely likes you as a person versus a client.
Years ago, my WL was a bubbly statuesque lady called Tori. We got on famously together and on three occasions, she stayed the night with me at a hotel on the city fringe.
Not a dive, a really nice place with a pool and sauna, the latter where we would sit in the steam and she would " let the girls out" while we kissed and cuddled.
On one occasion, we went as a couple to the Royal Show beforehand.
We'd have another session in the morning after breakfast before checking out and parting. All she ever charged me was $200 for a standard service whereas she could easily have charged $2000 for a dinner date and an overnight stay
Trust and friendship go a long way in the industry if you are fortunate enough to find them.