Lonnie, Although I haven't hunted the Gillette area, I would offer this advice. Since you want to do both deer/antelope, I would look at that northeast corner of the state if you can arrange a tresspass fee. Here is the reason.. Areas that have lots of public land, are very difficult for nonresidents to draw. I do not want to discourge you, but areas like Rawlins that have huge amts. of public land can even be difficult for residents to draw. Since you mentioned your friends age, he probably will not want to apply several years before getting a permit. Even then on the public sections he may not be successful.
I do know folks who drawn the ne section of the state very often, maybe even every year, due to the private land situation. I would contact the G & F. and get a list of land owners NOW..that allow tresspass hunting. Once your arrangements are made with him, you know you have a place to hunt, you are set... Any other information I could offer please don't hesitate to ask. This is what I would do if I wanted to hunt Wy. for sure next fall. I am even thinking of doing this myself for another years deer hunting.....