i 'only' have about 16K songs, around 150gb, and foobar doesn't even flinch. i don't much care for media monkey and wouldn't suggest trying it with such a massive library, but it's worth trying.
also remember that foobar is free, while media monkey charges for their best version.
not sure about playlists, it's been many years since i used itunes. but i assume you can save them in a standard format and import them just fine. i seem to remember having to do that with ratings, since itunes doesn't write them to tags. just made one playlist for 5-star, one for 4-star, etc. then imported them in foobar, redid ratings, and all was golden.
as for scripting - both apps require it if you want to go beyond what they give you out of the box. but you can get away without scripting easily enough, whichever app you choose.
i guess your best bet is to try both and see which one feels best for you!
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