BuffaloKyle

A week out is my usual for the first contact. If you want to message a provider say a month ahead of time don't book a slot and set it in stone. A lot can happen in a month, for both you and the provider, where if you would have to cancel or change the booking say a couple weeks later that it might ruffle some feathers. I'd keep it very brief with a month out message saying for instance "Hi. I'll be visiting Chicago the end of next month for work/leisure. Are you going to be in town that weekend and usually have availability on Fri or Sat evenings? If so please let me know your rate and once we get closer to my arrival we can make concrete plans."

Yes they will.

I don't mind getting quoted two different rates depending on an outcall vs incall. One provider recently that was based in Buffalo quoted a higher incall rate than outcall rate actually he said because he wanted to encourage outcall appointments. He had his own place but he didn't want every client to know where he lived and to not be giving out his address to guys who would then ghost him. Makes a ton of sense! I personally usually only hire when I know I'll be having my place to myself as I don't live alone and as I do prefer to host. Then if a provider has different rates I can go with the lower rate for either his place or mine.