I would much rather have a live and local host focusing on local issues.
But ask anyone who performs for a living, and they will tell you the goal is to reach more people. No matter how big he is in Boston, he's not going to get any bigger. The only way to demonstrate he's still growing and reaching more fans is to add more stations. He might do what Howie did and stay regional. That was he can still cover some local issues. But if you're on-air talent, and you're talented, you want to grow the audience. Obviously it's a big issue with him.