a $1000/hr hooker is going to gouge you on transportation?  I would recommend asking her if she plans to come by car, train, or helicopter, and then google prices so you have an idea of what to expect, at least within plus or minus $50.

but if you are asking her to travel, it's only right to compensate her for it. At least she isn't charging travel time.

 
I'll put it this way, if someone wants me to drill a well two hundred miles away, you're damn right I am charging extra for the time and expense of traveling.

 
What I always found amusing were the putas at the Del Rey who would ask for a "propina para taxi" afterwards when I knew damn well they were going right back downstairs looking for another date. I don't mind being generous, but I hate being hustled. lol

You have to estimate where she is coming from, or use the location stated in an Incall ad.  Offer a reasonable amount and in a polite way say take it or leave it.  If this figure does not cover what she needs, she will have to give you more detail on where she is coming from.

just go to New York..problem solved..

rates posted on their websites. Even if your particular gal doesn't, you can still use knowledge of what others charge to get a sense of what you're in for (assuming she isn't intent upon gouging you).

I'll either accept the travel cost without worrying about it, based upon past experience and market knowledge, politely ask for the approximate extra charge, or suggest a charge I know is consistent with the market.

It's clear from your post that when you "move on" you have success finding ladies with posted/known travel rates. WHy not just stick with them in the first place, and avoid the aggravation of the unknown pocket change haggler?

Depending where you are in NYC and where she is coming from, she might have to pass a few tolls on the way.  I've read NYC collects a million dollars in tolls every day.   That's a billion dollars every three years.  

Tell the provider that she will need to submit an itemized expense report for her travel costs, and once you have reviewed the receipts and checked her math, you will issue a check for that amount. Otherwise, this ridiculous business practice gets into some silly details, like you guessing low on the cost or her not being able to make change.

Here in the unsophisticated Midwest, ladies simply post a separate and usually higher rate for outcall. (A few charge more for incall than outcall because they don't have a reliable incall and need to get a hotel room.) Usually, the outcall rate is something like $50 or $100 higher, and the provider will only provide service within x number of miles.