I guess I am an adventurous soul....
I saw a provider on a Friday for lunch. Afterwards she asked me what I was up to and I said I was going to drive to Nawlins to go play...she asked if she could go..why not and we drove over there that night. She had never been and we had an absolute blast the entire weekend. I got hammered at the craps table and was shoveling chips to her and got so drunk she had to help me back to the room. I took in $8K and she accounted for every nickel. I think we had playtime once the entire weekend. Afterwards she never asked for anything and thanked me for the trip.
The following weekend, we went to Vega$. Had a blast again. Did not win anything, but saw great shows and ran the road. Her first trip out there. She got homesick so I had to send her home early which was ok. Afterwards we lost touch.
Same deal with another provider; saw her on Thursday and we took off to Nawlins on Friday and stayed up all night taking in the parades and Bourbon Street and worked our way back home casino hopping. Had a blast. Did not have playtime. We were having too much fun and kinda forgot about all of that.
The next time I met a provider on a Wednesday and asked her if she wanted to go to Nawlins and she agreed. I go to pick her up on Friday night after her last appointment and she asks if her daughter can go. Well, what the hell, why not. So her high school daughter goes with us. Now my car is a two seater convertible type so it was an uncomfortable drive but they made it work. The three of us had a blast. Of course, I put them up in their own room and there was no play time, but it was all about having fun.
Again, none of these providers asked for compensation (which I offered but they declined); I guess the trip was enough. I go first class!
Anyway, so when I do this, I think there are keys to success. Communication, Respect and Desire.
Always communicate what expectations are and what is working and not working. Respect each others space and privacy. And you must have a desire to make it work and to make it fun.
I do have one rule that I learned the hard way. If you do this, it's best to agree to be exclusive to one another during the trip. My ex wife went through about $20k one weekend...and I had to cut her off. So, she was turning tricks while I was either sleeping, at the spa or playing myself, so she could have more money to put in the slots. I found this out from my host. Needless to say, that pretty much ended that one!