Fans naturally wondered about a crossover with the original crew from the beginning. McCoy was in the pilot after all. But after encountering Sarek, Spock, and Scotty in later seasons, the big Kirk/Picard meetup felt a little forced.
Kirk's Nexus reality would have had a little poignancy had he been living happily with Edith Keeler, or his wife from The Paradise Syndrome. (Or Carol and David for that matter.) Instead, we got a girlfriend we never heard of, and the rest felt like a cheap plug for Shatner's horse farm. ;)
The way Picard's brother and nephew were killed off still seems incredibly random and cruel to me. (Who the heck dies in a barn fire in the 24th century?) The episode Family has been essentially ruined for me thanks to Generations.