Sleeping Arrangements: This is highly companion dependent. That said, here's my advice on how to look at this-do you snore and/or are you over 40? (IME, nearly every man over 40 snores, even if he's not aware of it.) If the answer is yes, then the question I would recommend you ask yourself is "How important is it to me that my companion is energetic, attentive, clear in mind and positive in mood during our waking hours together?" If this date is more than one night, then providing a separate room to sleep in ensures you have a companion who is far more likely to be precisely the dream girl experience you're paying for than a gal who is woken several times during the night (or doesn't get to sleep at all) from snoring or any other interruptions that can occur with a bed partner.
Rates/vacation: How would you feel if your job declared they should give you a pay cut because they're sending you to a convention in Las Vegas? Going to cool places is a perk of many jobs, but it's still work. Most companions have generous discounts for their time based on duration. (IE-per hour, a 3 day date is a much better deal than a 1 or 2 hour date.) A few providers will also openly offer additional discounts on their website for certain destinations or experiences, like bucket list items. Asking for discounts or trying to negotiate beyond what a provider has clearly written out is dicey waters-most companions will shut you down. If it's someone you know, (and I do strongly recommend you travel first time with a companion friend you know well,) you may damage the relationship. And, even if you get someone to say yes, I can assure you that you're not going to get the same experience as someone who demonstrated care and respect by paying in full and not trying to neg down her rates.
Attire: most of us generally try to match the culture of a place. We dress to turn heads, not raise eyebrows. South Beach is a pretty sex driven clothing culture, so she's more likely to dress more revealing there than she might in, say, Salt Lake City. But again, this is really provider dependent, so it's also based on her style and comfort level.
Overall, knowing a companion well before going on a travel adventure allows you to better know what you might expect, and to openly dialogue about your questions, concerns, and requests.
