Generally, the better you are on the radio, not fumbling or sounding insecure, the more often the controllers will feel like you know what you're doing and be okay with putting their job on the line with "Cleared in the Class Bravo"...
Remember, if you sound like you're going to screwup, they must keep you separated from the other traffic in there or they get pulled off the scope, the tapes get pulled, and they get to rack up a "deal" on their record.
Some Bravos just can't deal with you effectively. Vegas is notorious for it, but I've had Bravo clearances there. The problem in Vegas is lack of space inside the valley to set up a pattern for all the inbounds that keeps us little guys out of the way. They get nervous. They have to put airliners on collision courses with you at similar altitudes and then issue the correct vectors to turn them in. One timing glitch and it all goes down the tubes for them.
I've also heard that generally Chicago is a PITA but haven't experienced it personally yet. I can see why -- with the retarded levels of traffic United crams into O'Hare at bank time. In any weather, their push and everyone deviating around the weather is unreal.
Everywhere else, never had a problem. Just think about what you're going to say and speak clearly. It's really rare to get "Remain clear of the Bravo" forever. You'll still usually get a discrete squawk and they'll eventually be able to see your on-course desired path and work you into their flow somehow. The big hint that they really need you to go away is when they reiterate "Squawk VFR" in that same breath. That's the equivalent of Foghorn Leghorn's, "Go away kid, ya bother me!" line to the Chicken Hawk.
If they can, controllers will generally work with you. Just don't be off wandering around on headings or altitudes. It can make both your days go really badly. I never took it personally if they couldn't. That just meant that there was way too much high speed aluminum tubing wandering around over that direction and I probably didn't want to be over there anyway. A quick "thanks for your help" courtesy as you're leaving certainly never hurts either.