It's nice to hear from another bay area pilot! Of course ... you're moving east and I have been moving west
You bring up a good point and I know we have all, at one time, been made to feel as though we shouldn't have asked! I also know that Chicago can be difficult, but it is the exception and not the rule. More often than not I find the controllers around the country to accomodating. Even in the airspace surrounding LAX. I also find that if on the initial call the controllers suspect that you are inexperienced or might cause them problems, they will refuse. So the way the initial call is made can sometimes influence the outcome. Practice your Bravo transition communicaiton procedures until you sound like a professional and maybe even the Chicago controllers will let you through.
P.S I enjoyed the farm photos ... thanks!
"To Live is To Fly" - Townes VanZandt