Boy, that does sound like a tough situation. My DS is only 2 so I'm not in your shoes and don't have experience to offer, but I wonder about the fact that you say he's quite anxious and struggles with separation. I wonder if addressing his anxiety and issues with separation would indirectly help him to wean? If you see him struggling emotionally, he may benefit from some therapy with a child psychologist/psychiatrist. At 8 he really is on the tail end of the spectrum of nursing age and he should be near ready to wean. If he isn't, I wonder if he has some emotional issues that need attention. I'm not suggesting that extended nursing caused these issues, but maybe these issues are preventing him from moving on and letting go of nursing at an age when most children want to be "big kids"? Hope I haven't offended you. I think it's great that you're so willing to meet his needs.