Hello Mr newbie,
      Escorting is in some type of gray area in Toronto. It's the acts surrounding sex for pay, (for instance soliciting ,living off the avails, operating a brothel... Etc.) that are not legal.From my experiences, the money and intimate aspects of our meeting can be discussed in our email correspondence.

     I've never really had to deal with anyone talking about money during my dates. (unless they've counted wrong!). Accepting US dollars is at the discretion of the provider.  A good tip, would be to take a look at her website, usually there's an indication of whether or not she accepts US currency. usually a client just lays the envelope in plain sight for the lady to see upon entering the room.

      In terms of hotels, I would look for hotels without elevator keys access.  Depending on the type of provider you'd like to see just check her website or email her regarding what type of accommodation she expects you. Everyone is different!  

Do have fun! Don't be afraid to ask for fantasies to be fulfilled.

 
Hope that helps! Have a fun time in Toronto!