I suppose it depends on whether you are hosting or visiting the lady.  If you are the one hosting .. then lady would be going to the bathroom to freshen up and check envelope there

As a provider I can't say how common the "why don't you get comfortable *WINK WINK*" situation is, but I've never said such. I like unwrapping my presents and having my own unwrapped as well! In fact, I think it's kind of awkward to come back in the room and find someone naked (or mostly so).

I'd say that if you get the request, demur to it. It is a relatively small request, and there's no need to start off on the wrong foot. If you think you'd like to see her again, you can mention toward the end of the date that you'd prefer a slow undressing next time.

Even if she does ask you to do this, just politely let her know that while you're getting comfortable, you'd like her to remain dressed because you enjoy the unwrapping. I would also add that it's been a very rare occasion that a provider has asked me to go into the bathroom to disrobe and freshen. And, most providers have never even looked at the envelope while I've been there.  

My guess is that it all depends on the provider and her level of comfort with you.

This happens mostly on the first date and the escort wants you to disrobe without saying so.  In case you're the LE.

I've noticed that the girls are often eager to get you out of your clothes on the first date.  On subsequent dates things can relax and go at an easier pace.

I can't ever remember going into the bathroom to disrobe nor have I ever been asked to. In my experience "make yourself comfortable" means let's get naked!

Re: If she does ask or suggest...

that you get comfortable, there is nothing wrong with asking, "Wouldn't you like to help"? That also opens the door for you to help her as well.