Add multiple images – importing blogs from Roller

I recently bought wordpress hosting at GoDaddy and in the process of moving my blog (approx 950 entries) from Roller to there. Couple of questions …

1). My work folks generated a Movable Type Import format file from Roller but it does not have any entry for tags. It seems the format does not have a line entry for tags. How do I map my Roller tags to WordPress ?

2). My blog has several hundred of resource files. Manually uploading them is going to be *extremely* painful. It seems just copying the files to wp-content/upload is not enough. How do I mass upload the files, may be using a mix of ftp+ssh ?

Thanks,
-Arun