I'm about to port a smallish library from Java to Python and wanted some advice (smallish ~ a few thousand lines of code). I've studied the Java code a little, and noticed some design patterns that are common in both languages. However, there were definitely some Java-only idioms (singletons, etc) present that are generally not-well-received in Python-world.

I know at least one tool (j2py) exists that will turn a .java file into a .py file by walking the AST. Some initial experimentation yielded less than favorable results.

Should I even be considering using an automated tool to generate some code, or are the languages different enough that any tool would create enough re-work to have justified writing from scratch?

If tools aren't the devil, are there any besides j2py that can at least handle same-project import management? I don't expect any tool to match 3rd party libraries from one language to a substitute in another.