...I think that'd be a good guide on if you two can spend extremely long amounts of time together.  
Do you plan on taking breaks to do your own thing in Vegas or do you plan for the 2 of you to practically be attached to the hip?

with several regular friends...  
I rather meet the person first for a 2 hr, then a 6 hr date then we can discussed and consider a long weekend  trip. (overseas as well), it all depends of chemistry, if our personalities match.  

Can you imagine 48 hrs with someone you don't get alone with?! That's like a recipe for disaster.  

I love traveling with my regular friends...

As long as you are both compatible. Like ask her what is her idea of a fun Vegas trip. If it matches up with yours, GO! Ask her some questions. Like would she rather have her own room or is she cool sharing a bed with you all night. Some people prefer to sleep alone. Some people like a little time apart so that you don't get on each others nerves. Others don't need that time.  Ask her and just respect her opinions and thoughts and take it from there. That should help you decide a little easier. I hope.

 I have one client who I have been seeing for years. Met him when I was in Philly area and to this day we still get along. In fact we meet up for drinks and roulette at a casino in Baltimore. We have a ton of fun together.Its also just natural and relaxed. I could most definitely go to Vegas with hm.

Vacation vs trip to hell and back.

What the ladies have responded is spot on. You really need to spend a few hours and even include a food date, to see if you can tolerate the other person first. Been there done that several times hand have had opposite experiences. After several appointments , including lunches with a certain escort, I approached her about a weekend beach trip. It worked out so well, that we did it again several months later and that went well too.  On the other hand, I took a non-working girl that I barely knew, on a several day trip. It was her idea when she heard i was going. We found out soon that we had no compatibility. I liked loud music bars and go dancing. She liked it quiet, and wanted to read a book. I was thinking seeing I am paying for a room and the travel and food, that I was entitled to get laid (and multiple times too).  No she was going for the free ride and no affection.  Make sure you have the details ironed out in advance, and don't assume anything. If it is pay for play, know the price, and what is included. They may also ask to sleep in a separate bed. It can work out. But don't take sand to the beach.