Some questions you can find searching for the tags domain-driven-design or ddd here in SO. The book from Eric Evans also give some good insight of some situations you may face.
One important note is ddd is like tests, in the aspect that it increases development time of new features, but increase quality (and consequently, reduces development time in the long term). You might need constant contact with domain experts, so you can refine the model each time an issue appears.
IMHO, the most important issue of ddd is having a good, meaningful domain. Most issues (though not all of them) root problem is poor understanding of the domain
It is difficult to say what issues are the most common, as for every domain is a different domain, with its own peculiarities...