Location: Boulder, CO
1) OT2017 can connect to either IBGateway or GXTrader (Garwood server). NOTE: I had some unexplained behavior when using the IBGateway. I believe Barry is still investigating that problem. So, I'd advise using GXTrader, and make sure you have PreRelease 2M installed.
2) I run OT2017 in a VMware VM and also an Amazon Web Server for auto trading. I consider a Virtual Machine to be a more reliable environment than running on a PC where other things are also running.
3) Haven't tried this.