Smalltalk does have some advantages over Lisp, including the ones you mention. But lack of a good debugger isn't enough to make me switch. I like Lisp a lot. Besides, switching to Smalltalk would be more work than writing (modernizing, really) a Lisp debugger.
Just steal ideas from the Smalltalk debuggers. You can see their source. If you make a copy of the debugger, you can probably even debug and step through the copy debugger in the debugger.