1. most people don't make significant use out of the basic REPL. They use one integrated in to their editor/IDE. Emacs/Slime is probably the most popular, but I think there are addons for the Java IDEs too.
2. That may depend on what you're scraping. Manipulating semi-structured text data is one of Perl's biggest uses, so it may work a bit better than Clojure for the same purpose. Clojure certainly has decent regex and string capabilities though, so yes, it's a good choice.
3. Yes. There's a very good dataflow library for Common Lisp called Cells. It provides dependent and independent variables that work a lot like spreadsheet cells within a program. There's a partial port to Clojure. Also, Clojure has watchers - functions that can be attached to reference types and run whenever their state changes. Clojure and Common Lisp are quite fast at math, especially with type annotations.