I have two document libraries:
A set of document templates,
Work-in-progress proposals based on the templates, with required metadata to allow for documents to be categorized by client and project.
I would like my users to be able to use the OOB "Send To" functionality to move a copy of a template to the work-in-progress library.

I have two problems with the OOB SharePoint functionality. One:
Documents sent from one library to another do not automatically check in
If a user attempts to check in the file manually, they get an error regarding the metadata required by the library
I need a way to prompt the user for the required metadata and then check in. I know next to nothing about VB or programming, though I suppose I could learn quickly if need be.