Actually, I found some of the questions on Big Wally's list thought provoking. But I'd agree with whoever said that you'd probably want to bring up these subjects over a course of months.
I had a tough time ending a relationship a while back. The woman and I weren't compatible, and she had certain problems that would make it difficult for her to have a successful relationship with anyone. And she wasn't interested in dealing with those problems. As a result, I got some professional counseling that enabled me to end the relationship and get a better handle on how to go about recognizing desirable qualities in a partner. A book recommended by the counselor that was very helpful to me was "Are You the One for Me", by De Angelis. Now this book contains a lot of feminist garbage that's best ignored. But it also contains lists and exercises that are very helpful in determining whether you're compatible with a potential partner. If you just read the book, it's not going to do you any good. But if you treat it as a home study course, and make up the lists and complete the exercises, you'll get some good out of it. I came away from the book recognizing that my relationship with my ex wasn't going to work. Also, next time around, I know what to do and what questions to ask to increase the odds substantially that I'll be in a relationship that's going to last.