pour.rb

source_paths = ArchivablePathname.from(Dir.glob(File.join(options[:source], "*")))
Archiver.new(source_paths, destination)
        .move_unless { |path| File.exist?(File.join(destination, path.archive_path)) }
        .collect { |path| path.move = Prompts::ConfirmPrompt.ask(label: "File #{path.archive_path} exists. Overwrite?") }
        .move_if { |path| path.move? }

There's more context necessary (perhaps), but here's where this is going:

• Gathers a bunch of files from a source dir
• Factory method finds the archivable files
• Archiver moves the archivable ones that don't collide at the destination, returning an Archiver of just the collections
• Chained Archiver then prompts for user direction for each collision
• Chained Archiver then moves those that can be overwritten

Allowing a Force flag logic path, and likely a STDOUT logger, will be pretty easy after this.