Thanks guys. Yes Mizz I do have a knack for it I suppose. I have been around the world solo traveling a lot. Has been my one sober reprieve through the years. It's something I have been doing since I was a kid. I spent a year when I was young in the Dominican Repulic, went to Siberia (then Communist Russia) as a kid without my parents, and most recently lived in Central America and was happy there. I guess I felt like I gave it a "fair test" the last time I was down there. I came back here and have given this a "fair test" also. All things being equal I am leaning towards giving it a shot. I can rent out my Chicago APT to guests when I'm gone so I can keep my flat here. There's a lot of reasons I CANT do any of this too, but I think it is best to try and keep positive.
I obviously won't leave tomorrow but I will put a realistic plan in place and see if I can make it happen. Never hurts to try. If my effort fails then I'm safe and set here in Chicago with summer on the way and a renewed effort to socialize. I have to just start taking control of this stuff instead of watching everything go by.